Exchange 2010 to 2013 Migration: Authentication/Proxy Settings Issue

Question

I'm in the final stages of preparing for our Exchange 2010 to 2013 migration. I'm noticing minor authentication issues on mobile devices (android & ios) and proxy setting issues with Outlook that require user intervention. In an effort to make the migration
as smooth as possible for our internal users, I'd like to get these settings ironed out before starting the migration.
Symptoms:
Outlook - I'm aware that internal Outlook usage has changed its connection protocol from RCP/TCP to RCP/HTTP, but it appears that Outlook isn't updating its settings in the "Microsoft Exchange Proxy Settings" after a users mailbox has been migrated
from 2010 to 2013. Currently, 2010 users with Outlook 2013 have the following settings configured in Outlook's Exchange Proxy Settings:
URL to connect to my proxy server for Exchange: webmail.domain.com
Connect using SSL only: Checked
Only connect to proxy servers that have this principal name in their certificates: Unchecked
On fast networks, connect using HTTP first, then connect using TCP/IP: Unchecked
On slow networks, connect using HTTP first, then connect using TCP/IP: Checked
After migrating a user's mailbox from 2010 to 2013, the above settings remain the same in Outlook and their client disconnects from Exchange and isn't able to reconnect. After manually enabling the checkbox for "On fast networks, connect using HTTP
first, then connect using TCP/IP", Outlook clients are able to connect to Exchange via their newly migrated mailbox.
Is there a way to automatically updating these 2 proxy settings in Outlook during the migration instead of having to manually change each user's configuration in Outlook?
Android & iOS - Currently, users on Android & iOS with Exchange 2010 mailboxes have the following configuration:
domain: blank
username: their AD username
server: webmail.domain.com
After migrating a mobile users mailbox from 2010 to 2013, neither OS (Android or iOS) is able to connect due to an authentication failure. On iOS, if I manually change the domain from blank to my company's domain, authentication succeeds and their 2013 mailbox
begins to update. On Android, the option to change the domain name from null is grayed out, requiring the user to delete the Exchange profile and re-add it with the domain name intact. Is there a way to configure Exchange 2013 to not require the domain name
for mobile users in the same way that it's been working for us with Exchange 2010?
Please let me know if you require cmdlet print outs of my virtual directories to help troubleshoot the issue.

Answer 1

Hi,
Generally, when the user mailbox is moved from Exchange 2010 to Exchange 2013, the Autodiscover service would detect the changes and update the new configuration automatically.
Please make sure the autodiscover service in your new Exchange 2013 is configured correctly. We can create a new mailbox in Exchange 2013 and check whether the new Exchange 2013 user can setup account successfully in Outlook or not. If the new user works
fine, it indicates the autodiscover service in Exchange 2013 should be proper for internal user.
Please restart the following Exchange service to have a try:
Microsoft Exchange RPC Client Access
Microsoft Exchange Mailbox Replication
Restart IIS service by running IISReset in a Command Prompt window.
Then check whether the Outlook client can connect to Exchange 2013 or not.
As for Android & iOS issue, I suggest we can ask a question in ActiveSync forum for more suggestion:
https://social.technet.microsoft.com/Forums/en-US/home?forum=exchangesvrmobility
Regards,
Winnie Liang
TechNet Community Support