1
Jonathan Hassell
Ofce 365
Administrator’s Guide
2
Table of Contents
Chapter I
Connecting to Ofce 365
Creating New Users
Assigning Licenses
Blocking Users
Deleting Users
5 6 7 9 9
Provisioning Ofce 365 Accounts
Chapter II
Administering Exchange Online using the Graphical User Interface
Administering Exchange Online using PowerShell and the Command Line
10
17
Managing Exchange Online
Chapter III
Understanding the Default Site Structure
Administering SharePoint Online
Types of SharePoint Online Site Content
Best Practices for Structuring SharePoint Online
Understanding Groups and Permissions
Enabling Versioning
Managing SharePoint Online using PowerShell
Managing SharePoint Online
Chapter IV
Understanding the Dierences between SharePoint and OneDrive for Business
Administering OneDrive for Business
Confguring Storage Quotas
Managing OneDrive for Business
20
20
21
22
22
24
26
29
29
33
Guiding Users through the OneDrive for Business User Experience 33
3
Chapter V
Installing and Confguring Azure AD Connect
Setting Up a Hybrid Exchange Environment
Migrating Mailboxes from On-Premises Exchange to Ofce 365 in a Hybrid
Environment
Setting up a Hybrid Environment
35
37
39
Chapter VI
Encrypting Messages
Receiving and Responding to Encrypted Messages
Managing Encryption through PowerShell
Confguring Email Encryption
40
41
42
Chapter VII
Confguring Exchange Online Protection
Filtering Spam with Exchange Online Protection
43
Chapter VIII
Setting Up Ofce 365 DLP Policies
Viewing DLP Reports
Data Loss Prevention
45
49
Chapter IX
Safe Links
Safe Attachmentst
Spoof Intelligence
Using Advanced Threat Protection
50
51
53
Chapter X
Setting a Mailbox on Litigation Hold
Performing eDiscovery
Responding to Legal Requests
54
56
Understanding Bandwidth Requirements and Issues
Using the Service Health Dashboard
Using the Microsoft Remote Connectivity Analyzer
60
61
62
63
Chapter XI
Using Microsoft Support and Recovery Analyzer for Ofce 365
Troubleshooting Ofce 365 Issues
4
Useful Reference
About the Author
About Netwrix
Chapter XII
Creating Groups
Managing Ofce 365 Groups
Adding External Users to Groups
Using Ofce 365 Groups
64
65
66
68
70
70

5
I. Provisioning Ofce 365
Accounts
All users who consume Ofce 365 services need their own user accounts. In this chapter, I’ll cover how to set up these accounts quickly and efciently, assign the appropriate licenses to them, block accounts temporarily (for instance, when users are on
leave), and deprovision accounts when the users no longer require access to your
Ofce 365 tenant.
Chapter I | Provisioning Ofce 365 Accounts
Connecting to Ofce 365
The frst step in any of these tasks is to open a PowerShell session to Ofce 365 from
your local machine. I’ve created the script below to simplify this process; just copy it
into a text fle and save the fle with the extension .PS1. When you’re ready to connect,
go to the PowerShell console window and run the script by entering
.\scriptname.ps1
(that’s period, backslash, name of fle), and enter your Ofce 365 administrative credentials when prompted. Here’s the script:
$URL = “https://ps.outlook.com/powershell
$Credentials = Get-Credential -Message “Enter your Exchange
Online or Office\
365 administrator credentials”
$CloudSession = New-PSSession -ConfigurationName Microsoft.
Exchange -Connect\
ionUri $URL -Credential $Credentials -Authentication Basic
-AllowRedirection\
-Name “Office 365/Exchange Online”
Import-PSSession $CloudSession –Prefix “365”
The Prefx parameter in the last line of this script is important in hybrid deployments;
if you want to run this script in a purely cloud environment, you can remove the
-Prefx 365 part. The reason it’s needed in a hybrid environment is that sometimes
namespaces for cmdlets collide. For instance, if you were to run the New-Mailbox
command when you had Exchange Server running both locally and in Ofce 365,
PowerShell would not know whether to create the new mailbox locally or in the cloud.
To fx this, this script loads the Ofce 365 namespace of cmdlets with the prefx
“365”.
Therefore, you should name all your Exchange cmdlets that should run in the cloud
using the prefx
“365” (such as “New-365Mailbox” or “Get-365DistributionGroup”) and
leave all Exchange cmdlets that should run on your local deployment as they are by
default.This makes it very easy to tell them apart.
How to open a PowerShell session to Ofce 365 from your
local machine

Chapter I | Provisioning Ofce 365 Accounts 6
Creating New Users
Once you have connected to Ofce 365, you can create accounts either one at a time
or in batches.
To provision a single new Ofce 365 user, use the following script:
New-MsolUser -DisplayName "Employee Name Here" -FirstName
FirstName -LastName LastName -UserPrincipalName alias@
yourtenant.onmicrosoft.com –UsageLocation US
If the user is outside the United States, replace “US” with the appropriate two-letter ISO
country code. This is a required feld; you can’t assign licenses, which we cover in the
next section, until Ofce 365 knows which country your users will access their services
from. The user account will automatically be assigned a password, which will be displayed on the screen.
To provision multiple new Ofce 365 user accounts at the same time, frst create a CSV
fle with the following structure:
How to provision a single new
Ofce 365 user
UserPrincipalName,FirstName,LastName,DisplayName,UsageLocation
How to provision multiple new
Ofce 365 user accounts at the
same time
For example, here are three entries:
newuser1@yourtenant.onmicrosoft.com,John,Smith,John Smith,US
newuser2@yourtenant.onmicrosoft.com,Greg,Jones,Greg Jones,US
newuser3@yourtenant.onmicrosoft.com,Jacob,Rogers,Jacob Rogers,UK
Then use PowerShell to import the CSV fle and pipe the contents to the New-Msoluser
command, like this:
Import-Csv -Path "C:\newusers.csv" | foreach {New-MsolUser
-DisplayName $_.DisplayName -FirstName $_.FirstName -LastName
$_.LastName -UserPrincipalName $_.UserPrincipalName} –
UsageLocation $_.UsageLocation | Export-Csv -Path "C:\
newuserresults.csv"
The script will create the user accounts and also write a new CSV fle that lists the new
users along with the passwords that were automatically generated for them, which
you can then share with your users.

Chapter I | Provisioning Ofce 365 Accounts 7
Assigning Licenses
It’s not enough to create an account in Ofce 365; to be able to do anything, the account needs to have a license assigned to it. Dierent types of licenses “light up” different features of the service. You have 30 days after creating an account to assign a
license to it. You can generally mix and match licenses within a family, so some of your
users could have E3 plans, for example, while others have E1 and still others have E5.
Use the
Get-MsolAccountSku cmdlet to view the available licensing plans and
licenses in your organization, and use
Get-Msoluser to see the licensing status of all
users in your tenant.
To assign licenses, use the
Set-MsolUserLicense cmdlet. For example, to assign the
Ofce 365 Enterprise E3 plan (which shows up in PowerShell as
“ENTERPRISEPACK”) to
a user, use this command:
Set-MsolUserLicense -UserPrincipalName "newuser1@yourtenant.
onmicrosoft.com" -AddLicenses "yourorgname:ENTERPRISEPACK"
How to assign licenses to a user
To assign E3 licenses to all users who currently do not have a license assigned to them,
use the following two commands:
How to assign licenses to all users who don't have a license assigned to them
$UsersWithoutALicense = Get-MsolUser -All -UnlicensedUsersOnly
$UsersWithoutALicense | foreach {Set-MsolUserLicense
-AddLicenses "yourorgname:ENTERPRISEPACK"}
Directly from Microsoft in the Ofce 365 web portal. For most organizations, this
is the most direct way of purchasing services: You simply add a quantity of licenses
to your cart and buy them with a credit card, and then they’re generally immediately
available for use.
Through a volume licensing agreement. This method enables you to take advantage of organizational discounts, but it will take some time before you receive a code
for your licenses. Then you redeem the code on the web portal (there is no way to use
PowerShell to redeem licenses).
From a reseller. Sometimes it can be more cost-eective to purchase Ofce 365
through a reseller, who might o
er additional services like online backup or enhanced
spam fltering bundled with the core Ofce 365 o
ering. In this case, redemption of
licenses varies, but the reseller will walk you through the process.
You can acquire licenses for your organization in a few ways:
Where to Buy
Licenses
You can change and add licenses from the admin center GUI — just hover over “Billing”
and click “Purchase Services” and you’ll see the following screen (Fig. 1.1):
Chapter I | Provisioning Ofce 365 Accounts 8
Figure 1.1
Purchasing additional
licenses
In this guide, I’ll note which features require more advanced licenses. Some features
might well be sufciently compelling to convince you to upgrade to those licenses, at
least for a few users.
Figure 1.2
Changing the product
license for a user
Once you have purchased licenses, you can assign them to new users or existing
users. To change the license for an existing user, go to Users in the admin portal and
click the user’s name. Then, in the
yout menu, under Product licenses, click the Edit
hyperlink, as shown in the Figure 1.2.

Chapter I | Provisioning Ofce 365 Accounts 9
Blocking Users
If a user is on leave or otherwise temporarily away, you can block their account so no
one can use it. This is a good security precaution if you don’t want to delete a user account but the user won’t need it for an extended period of time. One PowerShell command will take care of it:
Set-MsolUser -UserPrincipalName newuser2@yourtenant.
onmicrosoft.com -BlockCredential $true
How to block a user account
To disable the block, use this command:
Set-MsolUser -UserPrincipalName newuser2@yourtenant.
onmicrosoft.com -BlockCredential $false
How to disable the block
Deleting Users
When a user leaves your company or no longer needs to use Ofce 365, you’ll want to
delete their account. PowerShell makes this easy, too:
Remove-MsolUser -UserPrincipalName newuser2@yourtenant.
onmicrosoft.com
How to delete a user account
In addition to removing the user account, this command automatically removes the
license assignment and puts the license back in your general pool so you can assign
it to another account in the future.

Chapter II | Managing Exchange Online 10
II. Managing Exchange Online
Exchange Online oers enterprise-class email, calendaring, and collaboration features.
Administrators can manage Exchange Online either using the graphical user interface
or using PowerShell and the command line. I’ll review both options.
Administering Exchange Online using the
Graphical User Interface
The web interface for Exchange Online is nearly identical to the web-based Exchange
Management Console (EMC) included in the on-premises product since Exchange
2013. While some parts of the Exchange Online EMC are specifc to Ofce 365, most
parts work exactly as you expect — for instance, you can create transport rules,
edit recipient settings to add new SMTP addresses, and establish and confgure
archive mailboxes.
Log in to
portal.ofce.com.
Click the wafe item in the top left corner.
Click
Admin.
Click the
icon in the left-hand pane of the resulting page.
Look for the icon with the
A on it, and hover over it.
From the resulting Admin Centers pop-out menu, click
Exchange.
This will get you to the Exchange admin center dashboard, as shown in Figure 2.1:
To access the Ofce 365 EMC, take the following steps:
1.
2.
3.
4.
5.
6.

Chapter II | Managing Exchange Online 11
Figure 2.1
The Exchange admin center
dashboard
Shared mailboxes are commonly used to allow multiple employees to access mail,
contacts, calendar items and related information stored in a single mailbox.
For instance, you might have a Customer Support mailbox associated with the
support@yourcompany.com address, which three employees are responsible for
monitoring.
To create a shared mailbox:
Go to the EMC.
On the Dashboard page, under the Recipients link, click
Shared.
Click the
+ icon, as shown in Figure 2.2.
Fill out the resulting form (Fig. 2.3), specifying the email address for the shared
mailbox and which users are allowed to view and send mail on behalf of the mailbox.
1.
2.
3.
4.
Creating a Shared
Mailbox
Figure 2.2
Adding a shared mailbox
Chapter II | Managing Exchange Online 12
Figure 2.3
Specifying the details of a shared
mailbox
Most organizations have multiple DNS domains for which they accept inbound email.
For example, you might have yourorganization.com, yourorganization.net and so on.
In order to get all of your domains working with Ofce 365, you need to set them up
in the service. There is a comprehensive wizard that walks you through identifying
your domains, verifying your ownership of those domains, and then setting up the
proper DNS records that will get other internet users to send trafc to your Ofce 365
tenant. For that wizard, go to
https://admin.microsoft.com/AdminPortal/Home#/
Domains
and then click the Add Domain button.
Specifying SMTP
Addresses for
a Recipient
Chapter II | Managing Exchange Online 13
In the EMC, go to the Dashboard page and click either Recipients (for an individual
user) or
Shared (for a shared mailbox).
On the resulting page, double-click the mailbox you want to modify.
Select
Email address from the options in the left pane of the pop-up menu.
Click the
+ icon to add a new email address, and enter the new email address in the
next window, as shown in Figure 2.4.
1.
2.
3.
4.
Figure 2.4
Adding an email address
to a mailbox
Once your domains are properly set up on your tenant, you can then add the
additional email addresses to each user.
In many organizations, principals and management have assistants or chiefs of sta
to
help manage their inboxes. In these cases, you need to grant other users permissions
to access the mailbox and/or send and receive mail on behalf of that user.
Here are the steps to take:
Granting Send
on Behalf and Full
Access Permissions
for a Mailbox
In the EMC, go to the Dashboard page and click either Recipients (for an individual
user) or
Shared (for a shared mailbox).
On the resulting page, double-click the mailbox you want to modify.
1.
2.

Chapter II | Managing Exchange Online 14
Figure 2.5
Adding Send As and Send on
Behalf permissions to a mailbox
Select Mailbox delegation from the options in the left pane of the pop-up menu.
Click the
+ button under “Send As” or “Send on Behalf” to add users with those capabilities for the mailbox (Fig. 2.5).
3.
4.
A distribution list is a single point of contact for a group of users. You might have a distribution list that includes all of a manager’s direct reports, another that includes all
employees in a company, and yet another with all users involved in a particular project.
Anyone can send email to the whole group by simply sending it to the distribution list.
Distribution lists are di
erent than Ofce 365 groups because they function only within
the context of email. Groups include a distribution list but also enable other functionality in applications like SharePoint, Microsoft Teams and so on.
To create a distribution list:
In the EMC, go to the Dashboard page and click
Groups.
On the resulting page, in the drop-down menu beside
“+ New Ofce 365 Group,”
select Distribution List.
1.
2.
Creating Distribution
Lists
Chapter II | Managing Exchange Online 15
Figure 2.6
Creating a distribution list
Fill in the page that pops up, specifying the name of the distribution list and the
users to be added to it.
3.
Mail ow (transport) rules are similar to the Inbox rules in Outlook; you can use them
to identify and take action on messages
owing through your Ofce 365 organization.
For example, mail claiming to be from executives and managers is often spoofed, so it
can be helpful to identify mail that originated outside of your organization. That way,
you can train your users to double-check that mail with sensitive instructions (like to
make a wire transfer or pay an invoice) comes from the real user and not some poser
outside the company.
To create a rule that stamps any message that originates from outside your organization:
In the EMC, go to the Dashboard page. Under
“Mail Flow,” click Rules.
Click the down arrow beside the
+ sign and choose Modify Messages from the
menu. (You can see here the other types of transport rules you can create.)
Fill out the resulting pop-up, as shown in Figure 2.7.
1.
2.
3.
Creating a Mail Flow
(Transport) Rule
Chapter II | Managing Exchange Online 16
Figure 2.7
Confguring a rule to mark
messages that originate from
outside the organization
There are a number of reasons, such as spam and user harassment, that users might
ask you to block certain outside senders from sending email to your organization.
To put folks on a tenant-wide block list, take the following steps:
In the EMC, in the
“Mail Flow” section, click Rules.
Click the
+ icon and then choose Create a new rule.
Name the rule, and then click
More options.
Under
“Apply this rule if,” choose The Sender.
Add the email addresses you want to block and then click
Check Names to put them
on the list.
Under
“Do the following,” choose Block the message and then click Delete the message without notifying anyone.
1.
2.
3.
4.
5.
6.
Blocking Senders
Chapter II | Managing Exchange Online 17
Archive mailboxes were introduced a couple of versions of Exchange ago to solve the
problem of tons of PSTs with old mail lying around in your network. Each mailbox has
an archive mailbox attached to it, where older mail can be retained on cheaper storage. That way, older mail is available for e-discovery, while the size of the primary mailbox is kept under control to improve performance.
To enable an archive mailbox in Ofce 365:
In the EMC, go to the Dashboard page and click either
Recipients (for an individual
user) or
Shared (for a shared mailbox).
Select the mailbox for which you want to enable an archive mailbox.
On the right, under
“In-Place Archive,” click Enable.
1.
2.
3.
Click More options, and then for the “Match sender address in message” option, select
Header or envelope.
Click
Save to fnish.
7.
8.
Administering Exchange Online using
PowerShell and the Command Line
Now I’ll show you how to use PowerShell to perform the same tasks we just saw how
to do using the Ofce 365 web interface. Be sure you’re connected to Exchange Online
PowerShell (as explained in Chapter I) and your session is ready.
Creating a Shared
Mailbox
The following command will create a new shared mailbox and give the account User1
access and Send on Behalf rights for that mailbox:
New-Mailbox -Shared -Name "Customer Support" -DisplayName
"Customer Support" -Alias support | Set-Mailbox
-GrantSendOnBehalfTo User1 | Add-MailboxPermission -User User1
-AccessRights FullAccessInheritanceType All
Enabling Archive
Mailboxes
Specifying SMTP
Addresses for
a Recipient
The following command adds three email addresses to a mailbox and makes
user1@yourdomain.com the default reply address for all mail sent out from that mailbox:
Set-Mailbox user1 -EmailAddresses “SMTP:user1@yourdomain.
com”,”user1@yourdomain.net”,”user1@yourdomain.org”

Chapter II | Managing Exchange Online 18
Granting Send
on Behalf and Full
Access Permissions
for a Mailbox
To grant George Caldwell access to Rita Bailey’s mailbox, use this command:
Add-MailboxPermission -Identity "Rita Bailey" -User "George
Caldwell" -AccessRights FullAccess -InheritanceType All
To allow George to send email on behalf of Rita (as if the email were coming from
Rita), use this command:
Add-RecipientPermission -Identity “George Caldwell”
-Accessrights SendAs -Trustee “Rita Bailey”
Creating Distribution
Lists
The following command creates a new distribution list with three members:
New-DistributionGroup -Name "Jon’s Direct Reports" -Members
edward@yourdomain.com,louann@yourdomain.com,rogelio@yourdomain.
com
To add or remove employees from a distribution list, use the following commands:
Add-DistributionGroupMember -Identity
"NameOfDistributionGroup\" -Member “usertoadd@yourorganization.
Remove-DistributionGroupMember -Identity "NameOfDistribution\
Group" -Member “usertodelete@yourorganization.org”
What if you need to create a new distribution group and then add a list of users to that
group? Perhaps there has been a reorganization and you need to recreate lists of direct reports, or there’s a new cross-departmental project with a lot of members and
you need to add 50 people to a list really quickly. PowerShell makes this easy indeed.
Emailaddress
user1@yourorganization.org
user2@yourorganization.org
First, you need a list of the email addresses in a CSV fle that looks like this:
The email addresses must already exist in your Ofce 365 tenant in order for this command to work.

Chapter II | Managing Exchange Online 19
$UsersToAdd = Import-CSV listofusers.csv
Then we’ll write a simple routine that iterates through that list and pipes each email
address to the Add-DistributionGroupMember command:
ForEach ($User in $UsersToAdd)
{
Add-365DistributionGroupMember –Identity “Test DG” –Member \
$User.emailaddress
}
Creating a Mail Flow
(Transport) Rule
Sometimes your legal team will require you to add a disclaimer to all outbound mail,
especially if your organization operates in a heavily regulated industry. Here’s how to
create the mail
ow rule you need:
New-TransportRule -Name ExternalDisclaimer -SentToScope
'NotInOrganization' -ApplyHtmlDisclaimerText "<h3>This is the
disclaimer heading</h3><p>Here is the text of the disclaimer.</
p><img alt='Corporate logo' src='http://www.yourdomain.com/
images/logo.png’>"
Enabling Archive
Mailboxes
The following command will enable an archive mailbox for user1:
Enable-Mailbox user1 –Archive
The following command will enable an archive mailbox for each user mailbox in your
Ofce 365 tenant:
Get-Mailbox -Filter {ArchiveStatus -Eq "None" -AND
RecipientTypeDetails -eq "UserMailbox"} | Enable-Mailbox –
Archive
First, we’ll establish a variable to hold the list of email addresses:
20
III. Managing SharePoint Online
SharePoint Online is designed to facilitate collaboration. Users can share documents,
calendars, lists, pictures, discussion boards and more with users both within your network and, in some cases, users outside of your network, such as partners or vendors.
Understanding the Default Site Structure
The basic unit of SharePoint content is the site collection — a group of sites with similar characteristics that can be managed as a whole. By default, your Ofce 365 subscription includes two site collections:
Chapter III |Managing SharePoint Online
A default team site collection, https://yourtenantname.sharepoint.com, which is
a basic SharePoint site designed for collaboration. You can create additional sites
in this site collection for individual teams, projects, meetings or whatever makes
sense for your organization.
A default public website collection,
https://yourtenantname-public.sharepoint.
com, which was originally designed to host the public-facing website for your company. This functionality is being deprecated, so I recommend ignoring this site collection.
In addition to those two tenant-wide sites, you also get individual
“My” sites for each
user in your tenant who has a SharePoint Online license. My site is essentially a front
end to the OneDrive for Business service and is where each user’s one terabyte of
storage space is found. This storage space can be synchronized to desktops and laptops so that a person’s documents are always on whatever device they are using. We
will talk more about OneDrive for Business later in this guide.
Administering SharePoint Online
You can access the SharePoint admin center by heading to https://
yourtenantname-admin.sharepoint.com
. You’ll be prompted to log in, and then you
will see

Chapter III |Managing SharePoint Online 21
Figure 3.1
The SharePoint admin center
Types of SharePoint Online Site Content
SharePoint Online has a defned list of content types that you can create on a given
site.
They include:
A page. A page is exactly what it sounds like — a page that is edited in the browser
using the editor functionality in SharePoint. Pages primarily contain text, but you can
embed images, links, lists, and web parts (little bits of code) in them.
A document library. A document library is a set of Word and other fles. You can
create folders to structure the documents logically within the library. To modify a fle,
a user must check it out and back in; this ensures that only one person edits a fle at
any given time and enables you to keep past versions so you can see the revision history of a given document.
Other kinds of libraries. There are form libraries that store XML forms which your
business can use to route information through Microsoft InfoPath; picture libraries
that store image fles; and wiki page libraries, which basically create a quick way to
edit text and have it remain on the web as well as link that text to other pages —
a poor man’s shareable text editor, you might say.
A site itself. Sites are basically collections of content, so you can create sites underneath your main SharePoint site (kind of like large folders on your fle system) to collect related materials that deserve their own focus. Meetings, blogs, documents, and
teams might have their own sites. If the hierarchy is confusing, think of it like this: A
site is a fle drawer in a fle cabinet, and the libraries, lists and other types of content
are the individual folders in that fle drawer.
A list. Lists are collections of like items. You can create a list of links, a list of announcements, a calendar, a list of contacts, a custom list in either list form or editable datasheet form, a discussion board, an issue tracking list, a list of project tasks (with
a Gantt-like chart), a survey, a task list, or an imported spreadsheet.

Chapter III |Managing SharePoint Online 22
Best Practices for Structuring SharePoint
Online
When you are frst starting with Ofce 365, it’s important to give some thought to how
you will structure your SharePoint sites. Most SharePoint experts recommend creating
site collections based on the types of permissions that users and creators will need.
For example, you might want to have separate site collections for sales and marketing,
customer support, research and development, and operations. Within each of those
site collections, you might give users permission to create subsites at will, so that
teams can manage their own sites and IT isn’t a bottleneck.
Understanding Groups and Permissions
Some of the most common administrative tasks are granting, modifying and removing
permissions from Ofce 365 users. The easiest way to understand SharePoint permissions is to compare them to standard NTFS permissions like you have in Windows —
groups of SharePoint users can have read and write (and some other SharePointspecifc) permissions granted to them.
You can see what permissions are available to grant on the ribbon of each SharePoint
site, on the Permissions tab:
Figure 3.2
Viewing permissions and groups
for the default SharePoint team
site in a tenant
On this page, you can create a new group; grant, edit or revoke permissions for the default groups (Team Site Members, Team Site Owners, and Team Site Visitors), or check
permissions on a specifc user or object.
If you click
Permission Levels in the Manage section of the ribbon, you can see all of the
permission levels available, as well as create or delete permission levels:

Chapter III |Managing SharePoint Online 23
Figure 3.3
Viewing and managing permission levels
If you want to create new groups of users so that you can assign them SharePoint permissions more granularly, the easiest option is to use the regular Ofce 365 admin
center. Since the entire service is based on Azure Active Directory, the groups you
create in one application are available for use in other applications, just as you would
expect if you created security groups in your on-premises Active Directory.
To create a new group:
Go to the administrative portal at
https://admin.microsoft.com/AdminPortal/
Home#/homepage
.
In the menu at the left, hover over the icon with multiple people. From the pop-out
menu, click
Groups.
Click
+ Add a Group.
Fill out the form to create a new mail-enabled security group. At this time, do not
create an Ofce 365 group — that is a di
erent type of group that is irrelevant to
our purposes right now. A mail-enabled security group is a group of users that
can be assigned permissions in various sites and services but that can also be addressed through a single alias like an Exchange distribution group could.
1.
2.
3.
4.

Chapter III |Managing SharePoint Online 24
Figure 3.4
Creating a new group
Enabling Versioning
One of the neat features of SharePoint Online is the service’s built-in support for versioning of documents. When versioning is enabled, SharePoint will create a new version of a fle each time it is saved. This makes it easy to create an audit trail, see who
made what changes and back out unwanted revisions. Most businesses that work on
sets of documents for long periods of time will fnd versioning helpful.
You enable versioning on document libraries. On a team site, for example, click
Documents, click the settings wheel at the top right of the window (within the black
bar) and then click
Library Settings. On the resulting page, under General Settings,
click
Versioning settings. You’ll see this page:
Chapter III |Managing SharePoint Online 25
Figure 3.5
Versioning settings for a document library
Make sure one of the versioning options — either “create major versions” or “create major and minor (draft) versions" — is enabled and click Save. Then, when your users are
creating, modifying and saving documents to that library, they’ll be able to see and use
di
erent versions in the history of the documents.
I recommend against enabling minor versions because every small change will generate a new version of the fle. While SharePoint is relatively efcient at storing fles,
you can quickly fnd your storage allotment eaten up with fles that add little value to
the versioning history. Unless you have a specifc need, stay with the
“Create major versions” option.
SharePoint automatically tracks the di
erent versions. Users can access them from the
web, but not directly from Microsoft Word, so instruct your users to head to the team
site document library when they need to see older versions. To see and edit di
erent
versions, click … next to a fle in a document library, and from the pop-up menu, select
Version history. You’ll see a screen like in Figure 3.6:
Figure 3.6
Accessing an older version of a
fle in a SharePoint Online document library
To edit a particular version, simply click the hyperlink.
26
Managing SharePoint Online using
PowerShell
You can manage the settings for most Ofce 365 applications using PowerShell. For
SharePoint Online, you need to download the SharePoint Online Management Shell
from the Microsoft website (
https://www.microsoft.com/en-us/download/details.
aspx?id=35588
) and then install it. If you’re running Windows 8.1 or Windows 10 on
your management workstation, that’s all you need. But if you’re still running Windows
7, you must also download and install the Windows Management Framework version
3.0 or later.
Run the SharePoint Online Management Shell and open a session to the admin site in
your tenant by entering:
Chapter III |Managing SharePoint Online
Connect-SPOService -URL https://yourtenant-admin.sharepoint.
com
You’ll be prompted for your tenant administrator credentials and then your session
will be loaded, like this:
Figure 3.7
Starting a new SharePoint Online
Management Shell session
To create a new SharePoint Online site, use the New-SPOSite command, specifying
a web address for the site, the user who will own the site and the storage quota in
gigabyes:
New-SPOSite -Url https://yourtenant.sharepoint.com/Sites/
newsitename -Owner you@yourtenant.com -StorageQuota 100
Creating and Populating Sites
Chapter III |Managing SharePoint Online 27
You can add a user to a site, but when you do, you need to add the user to one of the
existing site groups at the same time:
Add-SPOUser https://yourtenant.sharepoint.com/sites/
yoursitename -Loginname you@yourtenant.com -Group Visitors
One of the biggest draws of SharePoint Online is the ability to create extranet-like
functionality with a couple of clicks. For example, you can select to share a document,
document library, or even whole site with users external to your organization without
worrying (at least from the end user’s perspective) about federation, identity management, mapping credentials and all that jazz.
But some companies, especially those with more stringent or sensitive regulatory and
compliance requirements, want to completely disable the ability for external users to
access or even receive invitations to the content stored in their tenant. Luckily, one
command in PowerShell turns this ability on and o
.
To completely disable external sharing, use this command:
Set-SPOSite –Identity https://yoursite.sharepoint.com/sites\
/thesiteyouwant -SharingCapability Disabled
To enable both external user and guest (i.e., unauthenticated) access, use this command:
Set-SPOSite –Identity https://yoursite.sharepoint.com/sites\
/thesiteyouwant -SharingCapability ExternalUserAndGuestSharing\
To enable only authenticated external users (no guests) to have content shared with
them, use this command:
Set-SPOSite –Identity https://yoursite.sharepoint.com/sites\
/thesiteyouwant -SharingCapability ExternalUserSharingOnly
Confguring Sharing
To fnd out what groups are available on a site, use this command:
Get-SPOSiteGroup https://yourtenant.sharepoint.com/sites/
yoursitename

Chapter III |Managing SharePoint Online 28
$SitesToAudit = Get-SPOSite | Where-Object {$_.SharingCapab\
ility –ne “Disabled}
ForEach-Object ($Site in $SitesToAudit)
{
Write-Host $Site.URL “ has “ $Site.SharingCapability “ conf\
igured
Get-SPOExternalUserSiteUrl $Site.URL | Select DisplayName\
, Email, InvitedBy, WhenCreated | Format-Table –AutoSize
}
You will likely want to periodically review the current state of sharing on your tenant.
The following script will spit out sharing status and also who has received invitations
outside your organization for each site in your tenant:
Auditing Who Has
External Access to
a SharePoint Online
Site
29
IV. Managing OneDrive
for Business
OneDrive for Business is a fle storage and synchronization service that’s similar to
Dropbox: It makes all of an individual’s fles and folders available to them no matter
where they are or what device they are using.
Understanding the Dierences between
SharePoint and OneDrive for Business
Both SharePoint and OneDrive for Business enable users to store and share fles, and
access them from multiple devices. So when should users choose each solution?
Chapter IV | Managing OneDrive for Business
OneDrive. OneDrive is like a home directory or personal mapped drive where you
can save documents and retrieve them. While you can share fles from OneDrive with
others, it's really meant to be a personal repository of fles that can simply be synced
over many di
erent devices.
SharePoint. SharePoint, on the other hand, is ideal for projects that require collaboration with coworkers or people outside your organization. Having the project in a
SharePoint site makes it trivial to share information with colleagues and work on the
project together in real time. Essentially, if you own fles as a team and not as an individual, it generally makes sense to put them in a SharePoint site. Moreover, SharePoint
can handle additional types of content that OneDrive doesn’t support, such as calendars, wikis and meeting workspaces.
Administering OneDrive for Business
To customize how OneDrive for Business works in your Ofce 365 tenant, use the
OneDrive admin center at
https://admin.onedrive.com/?v=SharingSettings.
There you can confgure:
Sharing
Sync
Storage
Device access
Compliance
Notifcations

Chapter IV | Managing OneDrive for Business 30
On the Sharing page, you can choose the type of link that is generated when a user
shares a document. You can also confgure the number of days until a link expires and
whether links for fles have di
erent permissions than links that share the contents of
entire folders.
Pay particular attention to the external sharing options. You can control which, if any,
external users can access your OneDrive data. You can also set up a list of domains
with which sharing will be prevented; require users outside the organization accept an
invitation from the same account that the invitation was sent to (which prevents forwarding of invitations); and prevent external users from sharing items they don’t own.
Figure 4.1
Confguring external sharing
Sharing
From the Sync page, you can download the latest OneDrive sync client, which is recommended for Windows 7, Windows 8.1 and Mac clients — sync is built into Windows 10
and the Windows Update function will handle updating the client on those machines.
You can also prevent syncing of documents to users’ home PCs and blocking syncing
of specifc fle types, such as databases that might not sync well.
Sync
Chapter IV | Managing OneDrive for Business 31
Figure 4.2
Managing sync settings
On the Storage page, you can confgure the default quota for all users (from 1 to 5
terabytes), and also confgure the retention policy for documents that belong to
deleted users.
Storage
Figure 4.3
Managing storage quotas
Chapter IV | Managing OneDrive for Business 32
On the Device access page, you can restrict access to certain IP ranges (for example,
so that only devices on your ofce network can sync) or restrict access to devices that
support the latest authentication methods.
Figure 4.4
Managing device access
restrictions
Device Access
The compliance page is simply a shortcut to the Security & Compliance Center, which
Compliance I’ll cover later in this guide.
On the notifcations page, you can confgure how OneDrive notifes users and fle
Notifcations owners when things happen to their fles.
Figure 4.5
Confguring OneDrive for Business notifcations
Chapter IV | Managing OneDrive for Business 33
Confguring Storage Quotas
Each user with an Ofce 365 E type plan gets at least one terabyte of OneDrive for
Business storage. For E3 plans and higher with at least fve users, you get
“unlimited”
storage, but of course that’s not entirely true — you initially get one terabyte of space
per user, and the administrator can increase that quota to fve terabytes per user.
Once a user reaches the fve terabyte limit, you can fle a ticket with Microsoft support
to increase the quota to 25 terabytes per person. Once that limit is reached, further
space is apportioned to individual users as SharePoint team sites limited to a single
person.
You confgure storage quotas using the SharePoint Online Management Shell. To set
the default storage quota to 1TB, enter the following command:
How to set the default storage Set-SPOTenant -OneDriveStorageQuota 1048576
quota
For 5TB, I'll save you the math; it's 5242880. There is no free lunch here, though: If any
individual user's license doesn't allow for the value you specify here, their quota will be
set to the maximum value permitted by their license.
To reset an existing user's OneDrive to the new default storage limit, run the following
command:
Set-SPOSite -Identity /personal/jon_jonathanhassell_com
-StorageQuotaReset
How to reset an existing user's
OneDrive to the new default
storage limit
Guiding Users through the OneDrive for
Business User Experience
It’s easy for users to get started with OneDrive for Business — they simply log in to the
Ofce 365 portal at
https://portal.ofce.com and click the OneDrive button. The resulting page looks like this:
Chapter IV | Managing OneDrive for Business 34
Figure 4.6
OneDrive for Business web user
interface
Essentially, OneDrive for Business becomes another fle folder on the user’s system —
users can save fles, documents, spreadsheets, and everything else to the folder.
Figure 4.7
The OneDrive user experience
A circle with a green check mark, which means the fle exists both in the cloud and
on the local device.
Two arrows in a circle pattern, which means the fle is currently being synched.
A cloud icon, which means the fle exists only in the OneDrive cloud. To download
a permanent copy of a cloud fle to your local device, right-click the fle and choose
Always keep on this device.
The Status column for each fle will have either:

Chapter V | Setting up a Hybrid Environment 35
V. Setting up a Hybrid
Environment
Many organizations that use Ofce 365 have a hybrid deployment — that is, they also
have an on-premises Active Directory, which is the primary storage for identity information. To enable you to synchronize identity data from your on-prem AD to Azure
AD, Microsoft provides Azure Active Directory Connect, a fairly lightweight service that
runs on a server in your ofce or datacenter. You can select which objects to sync and
which objects to leave local.
There are two key facts that you should absolutely understand:
When you use Azure AD Connect to sync directories, you are creating what
amounts to an irrevocable relationship between your Ofce 365 tenant and your
local directory. You must create new users and make changes to your existing
users in your on-premises directory; you won’t be able to use the Ofce 365 GUI
or PowerShell to do it. While there are various hacks and unsupported ways of
breaking a sync relationship between an on-premises directory and Ofce 365,
you won’t be able to call for help when things go wrong. Expect that your tenant
will be forever bound to a local domain controller and that you will always have to
have that domain controller unless you migrate to a brand new tenant.
You don’t have to have a local Exchange Server to have Ofce 365 in directory
sync mode. But once you do create an Exchange hybrid relationship (this is
another step beyond directory sync; you’ll know it if you do it), you will have to
leave a single Exchange Server machine on your local network forever. This is
because of the way Ofce 365 defers some things to on-premises Exchange Server
machines; some roles that the on-prem machine holds cannot be moved up to
Ofce 365 in a supported way. Microsoft is working on changing this, so that when
all of your mailboxes are migrated to Ofce 365, you will decommission that last
Exchange Server on your network, but at this time, it remains a requirement.
Installing and Confguring Azure AD Connect
To use Azure AD Connect, take the following steps:
Download the Azure AD Connect installer from
http://go.microsoft.com/
fwlink/?LinkId=615771
.
Copy the installer to the server that you want to designate as the sync server
and run the installer.
1.
2.

Chapter V | Setting up a Hybrid Environment 36
Agree to the license terms and click Continue.
The Express Settings screen appears. Read the details of what the wizard will do,
and then, for the purposes of our walkthrough, click
Use express settings.
3.
4.
Figure 5.1
The Azure AD Connect Express
Settings screen
The Connect screen appears. Enter your Ofce 365 administrator's username and
password and then click
Next.
The wizard will do some computations and then show the Ready to confgure
screen. On this screen:
5.
6.
I recommend deselecting the “Start the synchronization process as soon as confguration completes” checkbox. You'll want to do some fltering of the directory
parts that get synchronized anyway, and when you uncheck this box, the
wizard confgures the sync service itself but disables the scheduler. Once you
have completed your fltering, you'll re-run the installation wizard in order to
enable the schedule.
If you are running Exchange locally, check the box to enable a hybrid Exchange
deployment. This will enable a few more directory attributes to sync, which will
serve you well when it's time to run the Exchange Hybrid Confguration Wizard,
as explained in the next section.

Chapter V | Setting up a Hybrid Environment 37
Click Install.
Once the installation completes, exit the wizard and reboot the machine.
7.
8.
It makes sense to sync only those directory objects that can be used in Ofce 365;
you don't want a bunch of service accounts and other objects littering your Azure AD
when there is literally nothing you can do with them in the cloud.
To customize which organizational units (OUs) are synchronized, take the following
steps:
Launch the Synchronization Service Manager.
Select
Connectors.
Open the properties of the Active Directory Domain Services connector.
In Confgure Directory Partitions, go to Containers. Enter your credentials to proceed.
Select the OUs you want to sync and then click
OK.
Last, you just need to enable the scheduler, which is just a standard Windows
scheduled task that has been disabled. To enable it, simply open Task Scheduler,
fnd the
"Azure AD Sync Scheduler" task, and then in the right pane under Selected
item, click
Enable. Wait until it runs (or run it immediately from the Task Scheduler
interface) and you'll see a bunch of new user accounts populating in Azure AD.
That's how you know the sync is working. You can also try logging on with one of
the accounts.
1.
2.
3.
4.
5.
6.
Setting Up a Hybrid Exchange Environment
If you are running Exchange on-premises, the next step is the fully enable the hybrid
relationship by confguring coexistence between your on-prem Exchange and
Exchange Online.
Take the following steps:
From the Exchange Admin Center, launch the Hybrid Confguration Wizard. In the
left pane, navigate to Hybrid and click
Enable.
Sign in with your Ofce 365 account.
1.
2.
Customizing What
Gets Synchronized
Click Accept. The Hybrid Confguration Wizard tool will be downloaded and install
itself automatically.
When the wizard has fnished installing, it will open. Click
Next to begin.
3.
4.

Chapter V | Setting up a Hybrid Environment 38
Figure 5.2
The Hybrid Confguration Wizard
Specify the Exchange Server machine you want to use or select the one that the
wizard has identifed automatically.
Enter credentials for your on-prem Active Directory deployment and for your Ofce
365 tenant.
The wizard will check the credentials. Once they've been verifed, click
Next
to continue.
For our purposes, choose the
Confgure my Client Access and Mailbox servers for
secure mail transport (typical)
option and click Next.
Choose the right SSL certifcates and click
Next.
Review all of the information you've entered and click
Update.
5.
6.
7.
8.
9.
10.
The wizard will run a number of PowerShell commands behind the scenes to confgure
your local Exchange Server machine and Ofce 365 tenant, make connectors, and confgure remote domains, encryption and so on.

Chapter V | Setting up a Hybrid Environment 39
Migrating Mailboxes from On-Premises
Exchange to Ofce 365 in a Hybrid
Environment
One of the benefts of a hybrid confguration is that you get a great way to migrate
your mailboxes to the cloud without having to pay for a third-party solution or do it
yourself manually over many long weekends.
To migrate mailboxes, take the following steps:
Open the Exchange Admin Center at
https://outlook.ofce365.com/ecp and choose
Migration in the recipients section.
Click the
+ icon, and then click Migrate to Exchange Online from the pop-up menu.
1.
2.
Figure 5.3
Migrating mailboxes in a hybrid
relationship
Select the remote move migration, and then click through the wizard. You'll add
a mailbox to a migration batch, create an endpoint if you need to and name the
batch. Tell the wizard where to contact you when the migration is complete, and
then wait for that email. Note that the migration could take hours, depending on
the size of your mailbox, the bandwidth and latency on your Internet connection,
and how busy Microsoft's Exchange Online servers are.
Launch Outlook on the migrated user's computer. Autodiscover should realize
the mailbox has been moved and do some reconfguration. Their phone or tablet
should also work with no user action required.
3.
4.

Chapter VI | Confguring Email Encryption 40
VI. Confguring Email Encryption
Ofce 365 includes powerful message encryption features that enable organizations to
securely send sensitive information across a heretofore relatively insecure infrastructure — mail servers. The E3 and E5 plans of the Ofce 365 and Microsoft 365 suites are
automatically licensed for encryption, and lower plans can use it if you add the Azure
Information Protection add-on license to those users. If your Ofce 365 tenant was
created after February 2018, then you automatically have the email encryption
capabilities present and turned on. If your tenant was created prior to that date,
Microsoft is slowly but surely rolling out the capabilities and enabling them for you;
they began this process in August 2018, so it should not be long before your older
tenant gets access.
Encrypting Messages
Users can encrypt any message they send. The procedure depends on which mail
client they are using.
Using the Outlook client, from the message window, go to the Options tab, click
Permission, and choose from the list of protection options.
Figure 6.1
Encrypting a message in Outlook
2016
In Outlook on the Web, in a new message window, click Protect in the menu bar, and
then click
Change permissions. In the window that pop ups, choose a protection option:
41
Figure 6.2
Encrypting a message in Outlook
for the Web
Chapter VI | Confguring Email Encryption
Receiving and Responding to Encrypted
Messages
When a user chooses to encrypt a message, the service will keep a copy of the message on its own servers and send a message to the outside recipient that looks like
this:
Figure 6.3
Receiving an encrypted message sent outside the Ofce 365
tenant

Chapter VI | Confguring Email Encryption 42
When the outside user clicks the “Read the message” button, they can either sign in with
an existing social account that uses the same email address as the message was sent
to, or they can choose to have the service send a one-time passcode to the same email
address. When either of those conditions is satisfed, the service will display the encrypted message in the web browser. The recipient can also reply securely to the original sender.
Managing Encryption through PowerShell
To verify that your tenant is set up for encryption, use the following command, making
sure the Sender value is a valid account within your tenant:
Test-IRMConfiguration -Sender someaccount@yourtenant.com
If you see “OVERALL RESULT: PASS” then you are ready to go.
When recipients of encrypted messages reply to those messages, you can set up a rule
that automatically strips the encryption from the reply so that your internal users don’t
need to sign in to the encrypted message portal to view the reply. (Since the reply
stays on the Microsoft servers, there is no risk of intercepting the message contents
in SMTP transit.) Use the following command:
New-TransportRule - Name "Strip encryption from inbound
e-mail" -SentToScope "InOrganization" -RemoveOME $true
How to verify that a tenant is set
up for encryption
How to set up a rule that automatically strips the encryption
from inbound emails

Chapter VII | Filtering Spam with Exchange Online Protection 43
VII. Filtering Spam with
Exchange Online Protection
Ofce 365 comes with an enterprise-class mail hygiene solution called Exchange
Online Protection (EOP). Mail sent to your organization is directed by your DNS MX
records to the EOP service, where it is scrubbed of spam, malware, unsolicited backscatter, phishing attempts and more; only then does it go to the Exchange servers
that make up the Exchange Online o
ering.
Confguring Exchange Online Protection
You can confgure EOP from the Exchange admin center at https://
outlook.ofce365.com/ecp/
. From the left menu, click Protection, and you’ll
see the various options and areas that EOP lets you adjust and customize:
Figure 7.1
Confguring EOP options in
the Exchange admin center
Each of the sections — malware flter, connection flter, spam flter, outbound spam,
quarantine, action center and dkim — has a default policy for your tenant. You can
either modify that policy or add new policies, some for a given set of recipients and
others for other groups of recipients.
The EOP service uses several di
erent antivirus engines to scan each message to ensure that your inbound mail stream is as free of viruses as is practically possible. You
likely don’t want to turn this o
, but you might want to adjust how notifcations are
provided to users when malware is detected. To adjust the settings, double-click the
malware policy and go to the Settings tab of the pop-up window.
Malware Protection
Chapter VII | Filtering Spam with Exchange Online Protection 44
If you have trusted systems sending email to your Ofce 365 tenant, you can add
their IP addresses to the list of trusted IP hosts so that mail coming from those systems won’t be subject to fltering. You might also be subject to real-time spam attacks
on rare occasions, and sometimes you can confgure flters on certain keys in those
attack’s message headers until the EOP system learns of the attack and is able to
respond intelligently.
Connection Filter
This is probably where you will spend the most time confguring EOP. When EOP
decides a message is spam, the default action is for it to send that spam to the user’s
Junk Email folder in Outlook. However, some organizations prefer a spam quarantine,
where likely spam messages are held for a period of time for manual inspection
until they expire and are deleted. If you prefer the quarantine approach, then it’s a
good idea to confgure quarantine notifcations for your users — the service will send
daily emails to users listing all the messages it held back because the service considered them spam, and users can release any false positives and ignore the rest.
Spam Filter
To set this up, take the following steps:
Double-click the default spam flter policy, choose
spam and bulk actions from the
left side of the pop-up menu, and then choose the
Quarantine option for the frst
two items:
1.
Figure 7.2
Confguring quarantine mode
for EOP spam fltering
Return to the Exchange admin center page. In the right pane, select Confgure
end-user spam notifcations
.
In the pop-up window that appears, check the
Enable box, select how often to send
quarantine notifcations (I recommend 1 so users will get them every day), and
then click
OK.
2.
3.
Spam in foreign character sets is a notorious problem, and while there is obviously nothing wrong with receiving mail in another language per se, if none of your sta
speaks a language, it doesn’t do you much good to receive email in that language. The
International Spam section of the spam flter dialog box lets you confgure which languages to receive.
International Spam
Notifcations
Chapter VIII | Data Loss Prevention 45
VIII. Data Loss Prevention
Data loss prevention (DLP) is an intelligent service that’s part of Ofce 365. It looks for
messages, fles, and objects that contain sensitive information and applies the policies
you confgure about what can and cannot be done with that data. The most common
types of sensitive information an organization would want DLP to look for are credit
card numbers, Social Security or insurance numbers, and other personally identifable
information (PII).
DLP uses pattern matching to determine whether text is likely to be sensitive information. When users try to interact with that data, the service applies the policies you confgured. For example, it might log an audit event for later review; display a warning
to the user saying, in e
ect, “hey, this looks sensitive; are you sure you want to be doing
that?”
; or block the action completely.
Setting Up Ofce 365 DLP Policies
In an Ofce 365 setting, it is best to confgure tenant-wide DLP policies that take into
account not just email but fles and text in SharePoint, OneDrive for Business and
other services as well. If you confgure DLP in the Exchange admin center, it will work
for email only; but if you set up the DLP policy in the right place, you get protection
across multiple services for no additional cost.
To set up tenant-wide DLP policies, take the following steps:
Go to the Security and Compliance center in the administrative portal at
https://
protection.ofce.com/?rfr=AdminCenter#/homepage
.
On the left, click
Data Loss Prevention, and then in the right pane, click Create a new
policy
.
Ofce 365 provides a number of pre-populated templates. For example, for U.S.
organizations, there are templates for detecting the following:
1.
2.
Data subject to the Gramm-Leach-Bliley Act (GLBA)
Data subject to the Payment Card Industry Data Security Standard (PCI-DSS)
United States personally identifable information (U.S. PII)
Data subject to the Health Insurance Portability and Accountability Act of 1996
(HIPAA)

46
Figure 8.1
Starting a new DLP policy
Chapter VIII | Data Loss Prevention
For our purposes, let’s click Financial and then U.S. Financial Data. Click Next.
Give the policy a name and description. Click
Next.
On the
“Choose locations” page, pick what parts of the Ofce 365 service this
particular policy will be enforced in. For this walkthrough, let’s choose
All locations.
Then click
Next.
On the next screen, you can customize the types of information this policy will
apply to. In most cases, you will want to accept the defaults, at least initially.
In this case, we’re looking for credit card numbers, U.S. bank account numbers
and routing numbers, and for our protection we want to know when this content
is attempted to be given to people external to our company. Click
Next.
3.
4.
5.
6.
Figure 8.2
Customizing the type of content
to protect with a DLP policy

Chapter VIII | Data Loss Prevention 47
Next, you’ll be asked what methods of enforcement you want to use. You can
choose to simply show policy tips to the user, which will just inform the user that
they’re working with sensitive information, or you can select to notify di
erent
people or block actions. For our purposes, let’s change the number of instances
required to 1 — even one credit card number leaked is too many these days —
and choose to block people from sharing the content. (If your business model
requires sharing of this type of sensitive data, you could use the DLP policy to automatically encrypt it before it is sent out; you’d just check the last box on this page.)
Click
Next.
7.
Figure 8.3
Confguring actions upon
triggering a DLP policy
On the next page, you can choose to block certain people from accessing
SharePoint and OneDrive for Business content and whether and how users
can override the DLP policy.
8.
Chapter VIII | Data Loss Prevention 48
Figure 8.4
Customizing access and
override permissions
Finally, you can choose whether to run the policy in test mode or begin enforcement immediately. I recommend using test mode for a while to make sure you
won’t adversely a
ect user workows. Test mode ags policy matches but doesn’t
actually prevent any content from being sent — it is like a
“what if” mode that
shows you what content would trigger a policy. You can also instruct Ofce to show
tips with Outlook while in test mode for user edifcation.
9.
Figure 8.5
Activating the policy
10. Review your settings and close the wizard.
Chapter VIII | Data Loss Prevention 49
Viewing DLP Reports
To understand how DLP aects your organization, you should review how often your
users tried to send content that matched a DLP policy. The Security and Compliance
center o
ers reports that show how often policies were matched over a period of
time. You can flter on policy matches that hit in Exchange, OneDrive for Business and
SharePoint, and you can also flter on severity, who the potential violator was and what
action was taken.
Figure 8.6
Report on DLP policy matches
Chapter IX | Using Advanced Threat Protection 50
IX. Using Advanced Threat
Protection
Viruses and malware use a variety of trajectories to infltrate organizations these days.
There is a premium service from Microsoft called Advanced Threat Protection (ATP)
that o
ers fve distinct features that add additional layers of security to your email
and documents. However, ATP is included only for users who are licensed for Ofce
365 Enterprise E5 plans. If you don’t want to upgrade everyone to an E5 package, you
can purchase ATP as an add-on license for US $2 per user per month.
Safe Links
The Safe Links feature of ATP guards against malicious links in both emails and Ofce
documents. It is similar to the
unifed threat management” of older edge-protection
and web-protection frewalls, in which the URLs users clicked on were intercepted by
the frewall and run through a scanning and hygiene process before the content was
allowed to come into the network. With Safe Links, email entering or leaving the organization goes through Exchange Online Protection (EOP), which flters spam and
phishing messages it knows about, and scans each message through a variety of antimalware detection engines.
When users click on links in messages that land in their inboxes, the ATP service
checks the link and does one of the following:
If the URL has been deemed by the ATP service to be safe, it is allowed to be
opened.
If the URL is on your organization’s
"do not rewrite" list, the website simply opens
when the user clicks the link. A
"do not rewrite" list is good for internal systems and
line-of-business applications that take certain actions based on URLs, like one-click
expense report approvals.
If the URL is on a custom block list that your organization confgured, a warning
page is displayed to the user.
If the URL has been deemed by the ATP service to be malicious in nature, a warning
page is displayed to the user.
If the URL goes to a downloadable fle and your organization's ATP Safe Links policies are confgured to scan such content, the ATP service will scan the fle before
downloading it.

Chapter IX | Using Advanced Threat Protection 51
Navigate to https://protection.ofce.com. Under Threat management, choose
Policy and then click Safe Links.
In the
“Policies that apply to the entire organization” section, select Default and then
click the pencil button to edit the policy.
In the
“Block the following URLs” section, you can add sites that no one in your organization ought to be able to visit. (This won't stop them from going to the site by directly entering its address into the address bar in their web browser, but it will prevent them from clicking a link in an email or document to visit it.)
In the
“Settings that apply to content except email” section, leave everything checked.
Click
Save.
1.
2.
3.
4.
5.
To modify your Safe Links policy, take the following steps:
When a user clicks a link in an email or Ofce document, they will see a message like
this:
Figure 9.1
How Safe Links notifes a user
that it is scanning a link
Safe Attachments
Scanning engines can miss new malware and viruses when they frst break out, before
they have been classifed and the signatures have been updated. With Safe Attachments, messages with attachments that don't match known signatures are sent to a
sandboxed virtual environment where they are securely opened. If the service detects
suspicious activity like a virus or malware trying to execute, the message is rejected or
quarantined. If no suspicious activity is detected, the message is released to the user.

Chapter IX | Using Advanced Threat Protection 52
Figure 9.2
Scanning attachments with the
ATP safe attachments service
Go to https://protection.ofce.com. In the left pane, under Threat management,
choose
Policy and then click Safe Attachments. Make sure that if you're presented
with the option to
"Turn on ATP for SharePoint, OneDrive, and Microsoft Teams," you
do so. (You'll want to allow at least 30 minutes for this to take e
ect across all of
Microsoft's global Ofce 365 datacenters.)
Click the
+ sign to create a Safe Attachments policy, and then enter a name and
description for the policy. The table below explains the available settings. I recommend dynamic delivery for most recipients. It’s the safest, it won’t delay the body
of an email, and it is virtually transparent to users who are not in front of their
computer all the time.
1.
2.
To confgure Safe Attachments policies, take these steps:
Chapter IX | Using Advanced Threat Protection 53
Spoof Intelligence
Spoof Intelligence spots mail with a From address (or with a sender feld in the headers of a message) that matches one of the domains confgured on your Ofce 365
tenant. Sometimes these messages can be legitimate — for example, you might send
a marketing newsletter from a separate service like Aweber or Mailchimp, or your
copier and scanner might send emails to your tenant and have a
“From” address in
your tenant. But other times it is someone impersonating an internal user in order to
trick people into sending a check to pay a fake invoice, initiate a foreign wire transfer
and so on.
Spoof Intelligence collects all the suspicious senders it detects in your mail
ow and
presents them in one convenient location, where you can decide which senders you'll
allow to send mail into your tenant and which ones should be blocked. To review this
list, go to the Security and Compliance page and click
Anti-spam settings.
Figure 9.3
Safe Attachments policy options
(image courtesy Microsoft Corporation)

Chapter X | Responding to Legal Requests 54
X. Responding to Legal Requests
For legal reasons, your organization might be required to hold on to the contents of
an employee’s mailbox account or produce all documents related to a case. Ofce 365
provides both litigation hold and eDiscovery capabilities.
Setting a Mailbox on Litigation Hold
A litigation hold suspends any retention policy or automatic deletion for a given mailbox so that no data can be removed from the mailbox. It preserves the original and all
modifed versions of each item, and even if a user deletes an item from their mailbox
using any version of Outlook, Ofce 365 retains the item for discovery purposes. The
user can continue to send and receive new mail. You can confgure how long the litigation hold lasts. At the expiration of that period, the hold will automatically be removed
and the existing retention policy (if any) that applies to the mailbox will be enforced.
If you’ve managed an Exchange on-premises installation, you might be familiar with
another type of hold, called
“in-place holds.” These holds are being deprecated and removed from Exchange Online, so the only hold that will be supported after the fall of
2018 will be the litigation hold, which was introduced with Exchange Server 2010.
To set a mailbox on litigation hold using PowerShell, open a session to Exchange
Online and then issue the following command:
Set-Mailbox mailbox@yourtenant.com -LitigationHoldEnabled
$true -LitigationHoldDuration 365
How to set a mailbox on litigation hold
To set a litigation hold on all mailboxes in your Ofce 365 tenant, use the following
command:
Get-Mailbox -ResultSize Unlimited -Filter
{RecipientTypeDetails -eq "UserMailbox"} | Set-Mailbox
-LitigationHoldEnabled $true -LitigationHoldDuration 365
How to set a litigation hold on all
mailboxes
Alternatively, you can use the web interface, but it’s obviously going to take a lot more
time to enable a litigation hold on multiple mailboxes than it takes to issue one
PowerShell command. But for one or two mailboxes, it is very simple:

Chapter X | Responding to Legal Requests 55
Navigate to the Exchange admin center at https://outlook.ofce365.com/ecp. From
the dashboard, select
recipients and then double-click the mailbox you want to put
on litigation hold. The following pop-up will appear:
1.
Figure 10.1
Putting a litigation hold on
a mailbox
Click mailbox features on the left, and then scroll down to where it says “Litigation
hold: Disabled.”
Click the Enable hyperlink. The following screen will appear:
2.
3.

56
Figure 10.2
Enabling litigation hold on a
mailbox through the Exchange
admin center
Chapter X | Responding to Legal Requests
In the frst feld, enter the number of days the litigation hold is to remain eective.
In the Note section, you can enter text that will be displayed to the end user in
a small display ribbon in the Microsoft Outlook client — it’s a good way to explain
to the user what’s happening and let them know that deleting an item does not
actually remove it. You can also enter a URL to an intranet or internet site that describes the hold, the reason behind it, details about the legal case or whatever your
communications team might want to say.
Click
Save and then Save again, and the litigation hold will take eect.
4.
5.
To disable the hold, follow steps 1 and 2, but in step 3, instead of clicking Enable, click
Disable. Then click Save.
Performing eDiscovery
Sometimes, administrators will be asked to fnd all materials that deal with a certain
keyword or keywords across your Exchange Online mailboxes, Ofce 365 groups,
Microsoft Teams, SharePoint Online and OneDrive for Business sites, and Skype for
Business conversations. To perform such a search, take the following steps:

Chapter X | Responding to Legal Requests 57
In the Security and Compliance Center, from the left menu, choose Search & Investigation, and then choose eDiscovery in the sub-menu. You’ll be presented with the
following screen:
1.
Figure 10.3
The eDiscovery portal in the
Security & Compliance Center
Click + Create a case to create a new eDiscovery case. This is how you manage the
holds, searches, and exports for each term; you separate them into cases so that
you can easily turn things on and o
, close cases that are complete, and track what
is happening with each search term. Give your case a friendly name and description, and then click
Save.
Your case name will then appear in the list; click
Open beside the case name to get
started confguring discovery actions.
1.
2.
In the eDiscovery center, cases are split into three actions:
Hold. To have a litigation hold automatically placed on all mailboxes, SharePoint sites
and public folders with content that matches certain keywords and conditions, click
Create and follow the wizard; it is fairly self-explanatory. The key screen on the wizard
is the one where you specify the query conditions. The fgure below illustrates how to
specify a keyword and a date flter to limit the scope of the search and resulting holds.
Figure 10.4
Specifying query conditions
Chapter X | Responding to Legal Requests 58
Search. You can save and run searches for keywords and other content, and you can
confgure search to search only through held locations, all locations or some custom
confguration. Since you can save these searches, you can start one, step away and
come back after it is complete. This is a good option for larger tenants.
Figure 10.5
Searching
Chapter X | Responding to Legal Requests 59
Export. The export area allows you to export the results of a search to a PST fle, which
you can then download and open on your own local computer or provide to counsel.
You can choose to export to a single PST fle or to one PST fle per mailbox, and the
output will be encrypted using a key that you choose. The wizard will walk you through
the steps required to export data.
Being able to globally search on whatever keyword you specify across all of the mailboxes in your tenant is a sensitive privilege that requires discretion and respect. Therefore, you need to assign a designated eDiscovery manager who will have permissions
to preview search results, export results and manage all aspects of the eDiscovery process. Choose this person wisely; they will have full access to every piece of data stored
in your tenant, regardless of other permissions that are set.
To designate an eDiscovery manager, take the following steps:
Assigning eDiscovery
Permissions
In the administrator portal, go to Security & Compliance, and then click the only
option in the left pane.
Scroll down to the eDiscovery Manager role and click the check box, and the popup window shown in Figure 10-6 will appear. Specify a user for the eDiscovery
Manager role and a user for the eDiscovery Administrator role — the latter needs
to have administrative privileges.
1.
2.
Figure 10.6
Designating an eDiscovery
manager

Chapter XI | Troubleshooting Ofce 365 Issues 60
XI. Troubleshooting Ofce 365
Issues
Issues with Ofce 365 can arise from problems with your local computers and connection, or problems with the Ofce 365 service itself. Microsoft oers tools to help you
troubleshoot both.
Using Microsoft Support and Recovery
Analyzer for Ofce 365
The Microsoft Support and Recovery Analyzer can run diagnostic tests to identif
and, in some cases, automatically resolve issues with local application confgurations.
To use the Support and Recovery Analyzer, download it from
https://
diagnostics.outlook.com/#/
. It will go through an installation process, prompt you
to accept a license agreement, and then present you with the main screen below:
Figure 11.1
Microsoft Support and Recovery
Assistant for Ofce 365

Chapter XI | Troubleshooting Ofce 365 Issues 61
Understanding Bandwidth Requirements
and Issues
One of the major pain points that some Ofce 365 users suer from is a lack of bandwidth — more specifcally, insufcient upstream bandwidth from the client site to the
nearest Microsoft datacenter. Enterprises with fast, dedicated fber connections can
have a vastly di
erent experience than a small ofce running over a 5 Mbps DSL circuit
over copper, for several reasons:
Regular use of Outlook eats up a lot of bandwidth. Outlook is a very chatty program,
and large attachments are still a preferred way of sharing documents and other fles.
Just two or three large attachments can saturate a 10 Mbps connection, which is a typical upload rate on business broadband connections these days.
Real-time audio and video conference demands a high-quality, low-latency connection. Skype for Business or Teams conferences both depend on enough bandwidth
to handle an uninterrupted stream of video trafc and a connection with low latency. (Bandwidth and latency are di
erent but related: Bandwidth is like how many lanes
there are on a highway, while latency is how long it takes a car to get from point A to
point B.) If your connection doesn’t satisfy either of these demands, then your users’
video and audio chats will be full of distortion and stutter.
Your initial migration of data to the service requires a lot of bandwidth. This is a
one-time thing. When you sign up for Ofce 365, you will almost certainly want to
bring your existing mail and calendar data into Exchange Online, or at least some subset of it. If you have 50 users and all of them have 4GB of mail, which would not be an
unreasonable assumption these days, then you need to upload 200GB of mail. At 10
Mbps, you’ll need nearly 49 hours of sustained upload. In reality, it’ll take much longer
due to connection overhead and the fact that, unless you manage the process well, all
of your clients will attempt to upload all of their data at the same time, causing throttling.
Microsoft o
ers some calculators that will help you understand what type of connection you need:
For Exchange, you can use the Exchange Client Network Bandwidth Calculator, available at
https://gallery.technet.microsoft.com/Exchange-Client-Network-8af1bf00.
This is an Excel spreadsheet that can help predict performance and suggest the
bandwidth you need based on your organization’s usage profle. You’ll want to know
statistics about your current usage, like your working hours, current bandwidth,
number of mobile devices, number of calendar meetings, average mailbox size and
size of your ofine address book (OAB).
For Microsoft teams and Skype for Business, you can use the Network Planner,
available at
https://myadvisor.fasttrack.microsoft.com/CloudVoice/NetworkPlanner,
to understand the di
erent sites and usage personas in your organization
and receive recommendations about how your network will perform under load.

62
As a rule of thumb, if your entire infrastructure is hosted in Ofce 365, all but the
smallest ofces will want a connection with at least 50 Mbps downstream bandwidth
and 10 Mbps upstream bandwidth.
Chapter XI | Troubleshooting Ofce 365 Issues
Using the Service Health Dashboard
If you suspect a problem with any of the components of the Ofce 365 service itself,
the frst place you should look is the Service Health Dashboard, available at
https://
portal.ofce.com/adminportal/home#/servicehealth
.
Figure 11.2
The Service Health Dashboard
If there are known issues with the servers that host your tenant (remember, Ofce 365
is a global service with millions of servers, so some users might see an issue while
others do not), you should see a notice in the dashboard. This doesn’t always happen,
especially right as an outage begins or if an outage is particularly severe and lots of
Microsoft hands are assigned to fx it, so it’s not a completely accurate system, but it
is a good place to start if you are experiencing service interruptions.
If you do see a relevant notice, you can click it to get more information.
Here is an example:
Figure 11.3
Checking a known issue posted
on the Service Health Dashboard

Chapter XI | Troubleshooting Ofce 365 Issues 63
Using the Microsoft Remote Connectivity
Analyzer
The Microsoft Remote Connectivity analyzer, available at https://
testconnectivity.microsoft.com/
, is a website hosted independently of the Microsoft
datacenter network. It can attempt to connect to various Microsoft services (or your
on-premises systems) in a variety of scenarios; a failure of any of these tests is a very
strong indicator that an issue resides on the Microsoft side of the equation and not
locally.
The Ofce 365 tab of the analyzer has a variety of tests, including tests to make sure
Exchange and Skype for Business Online are responding. You can also test inbound
and outbound email and, if you are operating in a hybrid environment, you can test
whether calendar free/busy results are available on the Ofce 365 side. If you are in
the initial stages of Ofce 365 adoption, you may also fnd it useful to try the Autodiscover tests to make sure your DNS records are properly entered and hosted so that
late-model Outlook clients can automatically fnd their own confgurations.
Figure 11.4
The Remote Connectivity
Analyzer

Chapter XII | Using Ofce 365 Groups 64
XII. Using Ofce 365 Groups
Ofce 365 groups enable users to access information in a variety of places, including
a SharePoint or OneDrive for Business document library, a OneNote fle, a shared
mailbox or calendar on Exchange, Lync or Skype for Business meetings, and data in
the Dynamics CRM database. Ofce 365 groups are objects in Azure Active Directory,
so they are not available in your on-premises deployment. This group identity includes
the users themselves, URLs for resources, who owns what groups, and what each
group’s membership list looks like.
Creating Groups
Both administrators and end users can create groups.
Ofce 365 administrators can log into the portal at
https://portal.ofce.com, click the
Admin link, hover over the people icon on the side, and then click Add Group.
Figure 12.1
Creating a group from the Ofce
365 portal

Chapter XII | Using Ofce 365 Groups 65
Users can create new groups directly from Outlook from the ribbon, as long as they
are using Outlook from the Ofce 365 ProPlus package:
Figure 12.2
Adding a new group from
Outlook
That will bring up a screen much like the portal’s screen, where they can name the
group and choose the privacy settings.
Figure 12.3
Creating a group from Outlook
Keep in mind that users can interact with Ofce 365 groups only from a web browser,
not from an Ofce desktop client. The upcoming Ofce 2016 client will include support
for groups, but that will require an upgrade of all of your clients.
Managing Ofce 365 Groups
Groups are intended to be largely self-service: Users can create their own groups and
administer their membership using tools built into the web user interface or through
the full applications in the Ofce 2016 suite. Users can also browse the list of groups
and sign themselves up to be members. Therefore, groups tend to proliferate quickly,
which leads to challenges for administrators, including the following:
Who manages the lifecycle of all of these groups, some of which might have been
created for week-long tasks and some of which are for long-term projects? Who
decides what content is still live and what needs to be archived?

66
What happens when the next iteration or version happens? How do accounts and
resources move around? The process is less than clear, particularly for users that
have a hybrid deployment of Exchange, SharePoint or both.
What if the topic being discussed in a group is sensitive? This group should
probably not be public, nor should just anyone be able to add themselves
to the group.
Chapter XII | Using Ofce 365 Groups
Adding External Users to Groups
One of the big benefts of Ofce 365 groups is the ability to let users outside of the
company collaborate on items in the group. Those capability centers around the concept of a guest user in Azure Active Directory, which is an account associated with an
email address from outside the tenant.
Only an owner of a group owner can add a guest to the group. Open the group
using Outlook Web Access on Ofce 365. From the three-dotted menu on the right,
select
Members and then Guests. Click Add Members and then enter the guest’s email
address.
Behind the scenes, Ofce 365 checks whether a guest user object already exists for
that email address; if it does not, Ofce 365 automatically creates one on the
y. Then
it grants the guest user appropriate permissions to the group and sends an email to
the guest user with a link to the object to be shared and information about how the
guest user can remove himself or herself from the group.
If the guest user has a Microsoft account that matches the email address the Ofce
365 users adds, then the guest will just authenticate with that. If not, then the user will
be pushed over to invitations.microsoft.com to begin the process of creating a special
ad-hoc account in that Ofce 365 tenant (which is not a universal Microsoft account).
What can a guest user do in an Ofce 365 group? Here are some common scenarios:
Join in a conversation in the group mailbox. This is through email only and not any
sort of interface on the Ofce 365 system; the messages are emailed to the guest’s
email address. Therefore, they can also search the group conversations they have
been a part of within their own mailbox.
Send meeting requests to the shared calendar for the group,
Interact with a single document in a SharePoint Online library that user has invited
them to edit.
Access the group’s document libraries now and search through those documents
in SharePoint Online using the Files view in Ofce 365.
See attachments sent through the OneDrive for Business integration with Outlook
and shared OneNote notebooks.

Chapter XII | Using Ofce 365 Groups 67
Giving external users access to corporate access raises two key concerns:
Risk of data loss — How do you make sure that users keep private content in the site
and don’t forward it or download it?
Risk of continued access — How do you ensure that access rights of external users
are consistently revoked when they are no longer needed?
Microsoft has built in some protections against these threats. For example:
Guests can interact with Ofce 365 groups only through the browser (except for
the individual email notifcations described earlier).
Guests can’t see Global Address List information, such as organizational hierarchy.
Guests can’t view or interact with information saved with Information Rights
Management (IRM) protection.
Guests don’t appear in the GAL.
Guests cannot become owners of Ofce 365 groups.
MailTips warn users of Outlook on the Web and the Outlook desktop client when
they are mailing items to a group that includes guest users to help prevent the
leak of confdential material.
To further mitigate these risks, you should educate your users about security best
practices for Ofce 365 groups, and require owners to regularly attest to the continued
usefulness and membership of their Ofce 365 groups.
Mitigating the Risks
of External Users in
Ofce 365 Groups
68
Useful Reference
Simplify management and streamline monitoring of your Ofce 365 environment with
the following resources:
Blog post | Ten Most Useful Ofce 365 PowerShell Commands
SysAdmin Magazine | Ofce 365: A 360° Perspective
Blog post | IT Trick: View Azure AD Sign-in Activity
Blog post | Ofce 365: Confguring User Passwords to Never Expire
Blog post | Using AD to Add an Alias to an Ofce 365 Email Account
Blog post | Best Tools for Management and Monitoring of Ofce 365
How-to | How to Detect Deleted User Accounts in Azure Active Directory
How-to | How to Stay on Top of Permissions Changes to Public Folders in Exchange Online
How-to | How to Detect Who Modifed Mailbox Permissions in Exchange Online
How-to | How to Detect Who Was Accessing Shared Mailbox in Ofce 365
Webinar | Tracking Changes in Hybrid Identity Environments with Both AD and Azure AD
Webinar | Top 5 Critical Exchange Online Events You Need Visibility Into
Blog post | Why Isn’t Native Ofce 365 and Azure AD Auditing Good Enough?
Quick reference guide | Azure AD Auditing
Quick reference guide | Exchange Online Auditing
Quick reference guide | Exchange Online Mailbox Auditing
SysAdmin Magazine | Danger in the Cloud
Research | 2018 Cloud Security Report
Webinar | A Hacker Explains: How Attackers Exploit Ofce 365 Vulnerabilities
Blog post | Security Tip: Enable Azure AD Self-Service Password Reset
Best practices | Password Policy
Manage
Monitor
Secure
69
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About Netwrix
About the Author
Jonathan Hassell is an expert in Microsoft products, including Azure AD and Ofce 365.
He has written several books on Windows Server and related products, regularly contributes to leading industry publications, and has spoken worldwide on topics ranging
from networking and security to Windows administration.
Netwrix Corporation is a software company focused exclusively on providing IT security and operations teams with pervasive visibility into user behavior, system confgurations and data sensitivity across hybrid IT infrastructures to protect data regardless
of its location. Over 10,000 organizations worldwide rely on Netwrix to detect and
proactively mitigate data security threats, pass compliance audits with less e
ort and
expense, and increase the productivity of their IT teams.
Founded in 2006, Netwrix has earned more than 140 industry awards and been named
to both the Inc. 5000 and Deloitte Technology Fast 500 lists of the fastest growing companies in the U.S.
For more information about Netwrix, visit
https://www.netwrix.com/.
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