Exchange Online by Chris Crandall on Dec 2018

Exchange Online – Change Primary SMTP Address

Purpose

The purpose of this blog is to validate the deployment and impact of changing the user’s primary SMTP address for a mailbox that is stored in Exchange Online. The test and validation tasks outlined in this document are performed using test accounts and test computers in a lab environment to simulate the services and their impact.

Lab Preparation

For the purpose of this testing scenario, there are two SMTP domains that will be used:

  1. CB5Lab.com
  2. CBfiveback.com

For this lab configuration, the necessary DNS records have been created for both SMTP domains, CB5Lab.com and Cbfiveback.com. The configuration of these DNS records will not be covered in this document.

Results

The major takeaway is the user had to either re-enter their username and password within Outlook or create a new Outlook profile (mixed results). On the mobile device, the user had to remove their profile from the Outlook app and reconnect to their mailbox.

User Sets

For the purpose of this testing, we will be using a set of two accounts:

Lenny@CB5Lab.com – Primary test account to test and validate service scenario and their impact.

Justin@CB5Lab.com – Account used to test mail flow to/from the primary test account

Test Cases

Validation Key Color Code

Test Case Color Code Key
Pass – no action required by the user
Fail – User required to re-enter their username and/or password
Fail – User required to remove e-mail profile and recreate

Outlook 2010

Test Case 001: Outlook Online Mode
Explanation Ensure the user is able to connect to their mailbox through Outlook 2010 after primary SMTP address is changed in online mode.
Pre-Configuration Actions
  1. Outlook 2010 profile has been created for test account (Lenny Paxton) in online mode.
Test Actions
  1. Change the primary SMTP address from Lenny@cb5lab.com to Lenny@cbfiveback.com
  2. Validate able to connect to Lenny’s mailbox through the Outlook 2010 client.
Comments from Test When launching Outlook after SMTP change for the test account, the account was prompted for credentials.
Test Results Test Date Result
8/6/2018 Fail

 

Test Case 002: Outlook Cache Mode
Explanation Ensure the user is able to connect to their mailbox through Outlook 2010 after primary SMTP address is changed in cached mode.
Pre-Configuration Actions
  1. Outlook 2010 profile has been created for test account (Lenny Paxton) in cached mode.
Test Actions
  1. Change the primary SMTP address from Lenny@cb5lab.com to Lenny@cbfiveback.com
Comments for Test When launching Outlook after SMTP change for the test account, the account was prompted for credentials.
Test Results Test Date Result
8/6/2018 Fail

 

Test Case 003: Delegate (Full Mailbox Permissions)
Explanation Ensure that after the user’s SMTP address is changed, user(s) with full mailbox permissions to this account. This test is to also ensure that any permissions this account has to other mailboxes are not impacted.
Pre-Configuration Actions
  1. Lenny Paxton has Full Access to Justin Kraft’s mailbox
  2. Justin Kraft has Full Access to Lenny Paxton’s mailbox
Test Actions
  1. Change SMTP address for Lenny Paxton
  2. Validate Lenny Paxton can still access Justin Kraft’s mailbox
  3. Validate Justin Kraft can still access Lenny Paxton’s mailbox
Comments for Test
Test Results Test Date Result
8/5/2018 Pass

 

Test Case 004: Delegate (Folder Permissions)
Explanation Ensure that after the users SMTP address is changed, folder permissions to the test account are not impacted.
Pre-Configuration Actions
  1. Lenny Paxton shared a folder for his mailbox with Justin Kraft
  2. Justin Kraft shared a folder for his mailbox with Lenny Paxton
Test Actions
  1. Change SMTP address for Lenny Paxton
  2. Validate Lenny Paxton is able to access the folder from Justin Kraft’s mailbox
  3. Validate Justin kraft is able to access the folder from Lenny Paxton’s mailbox
Comments for Test
Test Results Test Date Result
8/5/2018 Pass

 

Test Case 005: Send As Rights
Explanation Ensure that after a user’s SMTP address is changed that the Send-as permission(s) are not impacted.
Pre-Configuration Actions
  1. Lenny Paxton has Send-as rights to Justin Kraft’s mailbox
  2. Justin Kraft has Send-as rights to Lenny Paxton’s mailbox
Test Actions
  1. Change SMTP address for Lenny Paxton
  2. Validate Lenny Paxton is able to send as Justin Kraft
  3. Validate Justin kraft is able to send as Lenny Paxton
Comments for Test
Test Results Test Date Result
8/5/2018 Pass

 

Test Case 006: Send on Behalf
Explanation Ensure that after a user’s SMTP address is changed that the Send on behalf of permission(s) are not impacted.
Pre-Configuration Actions
  1. Lenny Paxton has Send on behalf rights to Justin Kraft’s mailbox
  2. Justin Kraft has Send on behalf rights to Lenny Paxton’s mailbox
Test Actions
  1. Change SMTP address for Lenny Paxton
  2. Validate Lenny Paxton is able to send on behalf of Justin Kraft
  3. Validate Justin kraft is able to send on behalf of Lenny Paxton
Comments for Test
Test Results Test Date Result
8/5/2018 Pass

 

Test Case 007: Update Calendar Entry (Another Mailbox)
Explanation Ensure any users that were able to update calendar entries prior to SMTP address change are still able to.
Pre-Configuration Actions
  1. Justin Kraft has been given Publishing Editor rights to Lenny Paxton’s calendar
  2. Lenny Paxton has been given Publishing Editor rights to Justin Kraft’s calendar
Test Actions
  1. Change SMTP address for Lenny Paxton
  2. Validate Lenny Paxton is able to create, edit, and delete calendar entries for Justin Kraft
  3. Validate Justin kraft is able to create, edit, and delete calendar entries for Lenny Paxton
Comments for Test
Test Results Test Date Result
8/5/2018 Pass

 

Test Case 008: Reply to an email sent to an internal recipient
Explanation Ensure that the users can reply to emails previously sent from internal recipients.
Pre-Configuration Actions
  1. Test account – Lenny Paxton has sent an email to Justin Kraft (internal account) prior to changing the SMTP address
Test Actions
  1. Change SMTP address for Lenny Paxton
  2. Reply to email previously sent to Justin Kraft (internal account)
Comments for Test
Test Results Test Date Result
8/5/2018 Pass

 

Test Case 009: Reply to an email sent to an external recipient
Explanation Ensure that the users can reply to emails previously sent from external recipients.
Pre-Configuration Actions
  1. Test account – Lenny Paxton has sent  an email to Justin Kraft (external account) prior to changing the SMTP address
Test Actions
  1. Change SMTP address for Lenny Paxton
  2. Reply to email previously sent to Justin Kraft (external account)
Comments for Test
Test Results Test Date Result
8/5/2018 Pass

 

Test Case 010: Reply to an email sent from an internal sender
Explanation Ensure that users can reply to emails sent from an internal mailbox prior to SMTP address change.
Pre-Configuration Actions
  1. Test account – Lenny Paxton has received an email sent by Justin Kraft (internal account) prior to changing the SMTP address
Test Actions
  1. Change SMTP address for Lenny Paxton
  2. Reply to email previously sent from Justin Kraft (internal account)
Comments for Test
Test Results Test Date Result
8/5/2018 Pass

 

Test Case 011: Reply to an email sent from an external sender
Explanation Ensure that user can reply to emails sent from an external mailbox prior to SMTP address change.
Pre-Configuration Actions
  1. Test account – Lenny Paxton has received an email sent by Justin Kraft (external account) prior to changing the SMTP address
Test Actions
  1. Change SMTP address for Lenny Paxton
  2. Reply to email previously sent from Justin Kraft (external account)
Comments for Test
Test Results Test Date Result
8/5/2018 Pass

Outlook 2016

Test Case 012: Outlook Online Mode
Explanation Ensure the user is able to connect to their mailbox through Outlook 2016 after the primary SMTP address is changed in online mode.
Pre-Configuration Actions
  1. Outlook 2016 profile has been created for test account (Lenny Paxton) in online mode.
Test Actions
  1. Change the primary SMTP address from Lenny@cb5lab.com to Lenny@cbfiveback.com
  2. Validate able to connect to Lenny’s mailbox through the Outlook 2016 client.
Comments for Test When launching Outlook after SMTP change for the test account, the account was prompted for their credentials
Test Results Test Date Result
8/6/2018 Fail

 

Test Case 013: Outlook Cache Mode
Explanation Ensure the user is able to connect to their mailbox through Outlook 2016 after the primary SMTP address is changed in cached mode.
Pre-Configuration Actions
  1. Outlook 2016 profile has been created for test account (Lenny Paxton) in cached mode.
Test Actions
  1. Change the primary SMTP address from Lenny@cb5lab.com to Lenny@cbfiveback.com
Comments for Test When launching Outlook after SMTP change for test account, the account was prompted for their credentials
Test Results Test Date Result
8/5/2018 Fail

 

Test Case 014: Delegate (Full Mailbox Permissions)
Explanation Ensure that after the users SMTP address is changed, users with full mailbox permissions to this account and permissions this account has to other mailboxes are not impacted.
Pre-Configuration Actions
  1. Lenny Paxton has Full Access to Justin Kraft’s mailbox
  2. Justin Kraft has Full Access to Lenny Paxton’s mailbox
Test Actions
  1. Change SMTP address for Lenny Paxton
  2. Validate Lenny Paxton can still access Justin Kraft’s mailbox
  3. Validte Justin Kraft can still access Lenny Paxton’s mailbox
Comments for Test
Test Results Test Date Result
8/5/2018 Pass

 

Test Case 015: Delegate (Folder Permissions)
Explanation Ensure that after the users SMTP address is changed, folder permissions to this account are not impacted.
Pre-Configuration Actions
  1. Lenny Paxton shared a folder for his mailbox with Justin Kraft
  2. Justin Kraft shared a folder for his mailbox with Lenny Paxton
Test Actions
  1. Change SMTP address for Lenny Paxton
  2. Validate Lenny Paxton is able to access the folder from Justin Kraft’s mailbox
  3. Validate Justin kraft is able to access the folder from Lenny Paxton’s mailbox
Comments for Test
Test Results Test Date Result
8/5/2018 Pass

 

Test Case 016: Send As Rights
Explanation Ensure that after a user’s SMTP address is changed that the Send-as permission(s) are not impacted.
Pre-Configuration Actions
  1. Lenny Paxton has Send-as rights to Justin Kraft’s mailbox
  2. Justin Kraft has Send-as rights to Lenny Paxton’s mailbox
Test Actions
  1. Change SMTP address for Lenny Paxton
  2. Validate Lenny Paxton is able to send as Justin Kraft
  3. Validate Justin kraft is able to send as Lenny Paxton
Comments from Test  
Test Results Test Date Result
8/5/2018 Justin Kraft Pass

 

Test Case 017: Send on Behalf
Explanation Ensure that after a user’s SMTP address is changed that the Send on behalf of permission(s) are not impacted.
Pre-Configuration Actions
  1. Lenny Paxton has Send on behalf rights to Justin Kraft’s mailbox
  2. Justin Kraft has Send on behalf rights to Lenny Paxton’s mailbox
Test Actions
  1. Change SMTP address for Lenny Paxton
  2. Validate Lenny Paxton is able to send on behalf of Justin Kraft
  3. Validate Justin kraft is able to send on behalf of Lenny Paxton
Comments for Test
Test Results Test Date Result
8/5/2018 Pass

 

 

Test Case 018: Update Calendar Entry (Another Mailbox)
Explanation Ensure that after a user’s SMTP address is changed they are still able to update other user’s calendar they were given access to.

Ensure that after a user’s SMTP address is changed, any user’s with the ability to update their calendar can still do so.
Pre-Configuration Actions
  1. Justin Kraft has been given Publishing Editor rights to Lenny Paxton’s calendar
  2. Lenny Paxton has been given Publishing Editor rights to Justin Kraft’s calendar
Test Actions
  1. Change SMTP address for Lenny Paxton
  2. Validate Lenny Paxton is able to create, edit, and delete calendar entries for Justin Kraft
  3. Validate Justin kraft is able to create, edit, and delete calendar entries for Lenny Paxton
Comments for Test
Test Results Test Date Result
8/5/2018 Pass

 

Test Case 019: Reply to email (internal recipient)
Explanation Ensure that the user can reply to emails previously sent from internal recipients.
Pre-Configuration Actions Test account – Lenny Paxton has sent an email to Justin Kraft (internal account) prior to changing the SMTP address
Test Actions
  1. Change SMTP address for Lenny Paxton
  2. Reply to email previously sent to Justin Kraft (internal account)
Comments for Test
Test Results Test Date Result
8/5/2018 Pass

 

Test Case 020: Reply to email (external recipient)
Explanation Ensure that the user can reply to emails previously sent from external recipients.
Pre-Configuration Actions Test account – Lenny Paxton has sent an email to Justin Kraft (external account) prior to changing the SMTP address
Test Actions
  1. Change SMTP address for Lenny Paxton
  2. Reply to email previously sent to Justin Kraft (external account)
Comments for Test
Test Results Test Date Result
8/5/2018 Pass

 

Test Case 021: Reply to email (internal sender)
Explanation Ensure that user can reply to emails sent from an internal mailbox prior to SMTP address change.
Pre-Configuration Actions Test account – Lenny Paxton has received an email sent by Justin Kraft (internal account) prior to changing the SMTP address
Test Actions
  1. Change SMTP address for Lenny Paxton
  2. Reply to email previously sent from Justin Kraft (internal account)
Comments for Test
Test Results Test Date Result
8/5/2018 Pass

 

Test Case 022: Reply to email (external sender)
Explanation Ensure that user can reply to emails sent from an external mailbox prior to SMTP address change.
Pre-Configuration Actions Test account – Lenny Paxton has received an email sent by Justin Kraft (external account) prior to changing the SMTP address
Test Actions
  1. Change SMTP address for Lenny Paxton
  2. Reply to email previously sent from Justin Kraft (external account)
Comments for Test
Test Results Test Date Result
8/5/2018 Pass

iOS Devices

Test Case 023: Outlook app
Explanation Ensure that user can connect to their mailbox through the iOS Outlook app after their SMTP address is changed
Pre-Configuration Actions
  1. Users profile has been created on the Outlook app for an iOS device
Test Actions
  1. Change SMTP address for Lenny Paxton
  2. Open Outlook app to test connection
Comments for Test Outlook was not able to reconnect to the user’s mailbox. The user was prompted to remove the account and add the account to the app.
Test Results Test Date Result
8/5/2018 Fail

 

Test Case 024: Native app
Explanation Ensure that user can connect to their mailbox through the iOS native mail app after their SMTP address is changed
Pre-Configuration Actions
  1. Users profile has been created on the iOS native mail client
Test Actions
  1. Change SMTP address for Lenny Paxton
  2. Open iOS native mail client to test connection
Comments for Test
Test Results Test Date Result
8/5/2018 Pass

Android Device

Test Case 025: Outlook App
Explanation Ensure that user can connect to their mailbox through the Android Outlook app after their SMTP address is changed
Pre-Configuration Actions
  1. Users profile has been created on the Outlook app for an Android device
Test Actions
  1. Change SMTP address for Lenny Paxton
  2. Open Outlook app to test connection
Comments for Test
Test Results Test Date Result
8/5/2018 Pass

 

Test Case 026: Native App
Explanation Ensure that user can connect to their mailbox through the Android native mail app after their SMTP address is changed
Pre-Configuration Actions
  1. Users profile has been created on the Android native mail client
Test Actions
  1. Change SMTP address for Lenny Paxton
  2. Open Android native mail client to test connection
Comments for Test
Test Results Test Date Result
8/5/2018 Pass

Supporting Services

Test Case 027: Skype for Business
Explanation Ensure that user can connect to Skype for Business client after their login has changed
Pre-Configuration Actions
  1. Setup login information on the client prior to changing login information
Test Actions
  1. Change user’s login information
  2. Test logging into Skype for Business client
Comments for Test User’s login was not transparent, the user was prompted for username and password and was then able to login.
Test Results Test Date Result
8/5/2018 Fail

 

Test Case 028: OneDrive for Business
Explanation Ensure users can access their OneDrive for Business after their UPN is updated.
Pre-Configuration Actions
  1. OneDrive for Business is synced on the client computer.
Test Actions
  1. Updated UPN for test user account.
Comments for Test User account was prompted to re-enter credentials to sync OneDrive for Business folder.
Test Results Test Date Result
4/8/2016 Fail

 

Test Case 029: Outlook Add-ins
Explanation Ensure Outlook add-ins work after the user’s SMTP address has been changed.
Pre-Configuration Actions
  1. Outlook add-ins enabled (Skype for Business add-in & Adobe PDFMaker tested)
Test Actions
  1. Change user’s SMTP address
  2. Tested Skype for Business Meeting & Adobe PDFMaker
Comments for Test
Test Results Test Date Result
8/5/2018 Pass

 

Test Case 030: Outlook Web App (OWA)
Explanation Ensure user is able to access their mailbox through OWA after their primary SMTP address has been changed.
Pre-Configuration Actions
Test Actions
  1. Log into OWA
Comments for Test
Test Results Test Date Result
8/5/2018 Pass

 

Test Case 031: Outlook Web App (OWA) Offline Mode
Explanation Ensure that user can access their mailbox in offline mode after their SMTP address has been changed.
Pre-Configuration Actions
  1. Log into OWA and setup offline mode
Test Actions
  1. Change SMTP address for user’s email address
  2. Log into OWA
Comments for Test
Test Results Test Date Result
8/5/2018 Pass