Unable to connect using Outlook for Android with IMAP and double-quote in password

[HumanIMDB (Chris Rivers)]

After struggling with this for months, I believe I have finally have workarounds for the issue.

Symptoms included:

• Unable to access an IMAP account in Outlook for Android (OfA) after application update via Play Store ; no account changes made
• Unable to authenticate to IMAP server after performing OfA reset (clear cache, clear storage, uninstall, reinstall) ; username and password work correctly via webmail and exact settings work in Outlook on PC
• Set secure ports for IMAP (993) and SMTP (465) and receive a username/password authentication error ; username and password work correctly via webmail and exact settings work in Outlook on PC (Issue #1 )
• Complex password not working in OfA ; username and password work correctly via webmail and exact settings work in Outlook on PC (Issue #1)
• Able to setup IMAP account in OfA but unable to open messages, application crashes, folders open without displaying messages, etc; everything continues to work properly in Outlook for PC ( Issue #2 )

Issue #1

While troubleshooting the issue I ran the IMAP Email Connectivity Test from Microsoft as the issue was presenting as a certificate issue.

https://testconnectivity.microsoft.com/ → Exchange Server → IMAP Email.

Certificate validation displayed a warning but the actual failure was failing on login with “2 BAD Invalid characters in atom”

Workaround #1: I simplified the password to contain only upper and lower case letters and numbers.

Reference articles:

Unable to connect using Outlook for Android with IMAP and double-quote in password

NethServer Version: 7.8.2003 Module: dovecot I have a user that uses Outlook on Android to access the mail and it stopped working last Friday and I suspect at the same time that I installed the latest updates including nethserver-mail-*. When I looked in the logs it says something about disconnecting the user because no password was sent. The version of Outlook is 4.2045.1 and the password length is over 90 characters. It works fine with the Gmail-app and also with Webtop. Which logs should I…

Issue #2

With the account setup in OfA, I was able to access the mailbox however there were still significant issues and OfA was virtually unusable.

Believing this was likely an issue with an update to the application as these issues started after an application update, I tested the app with the working settings every time the application was updated without any change in the issue.

Finally, I found a thread where someone was having the same/similar issue and they changed the SMTP port to 587.

With SMTP port set to 587, OfA is functioning normally.

Workaround #2: Set SMTP port to 587 not 465.

Conclusion:

Neither of these issues have been resolved, I have simply been able to work around these issues to get OfA to work.

Outlook on PC continues to work with IMAP 993 and SMTP 465 and with a complex password set for the account.

[Andy_Wismer (André Wismer)]

@HumanIMDB

Hi Chris

Just for your info: Nobody should be using an unofficial port for mail like 465. This is NOT in the RFCs and was intended only as a temporary workaround.

It’s long outlived it’s purpose, but a lot of providers still support that (besides 587 and a lot also 25).

Unfortunately, a lot of people still have that unofficial port in their head…

Nowadays most SMTP servers allow you to use 25 and 587 (official), NethServer will also allow 465, but as said, why should anyone still use that?

Port 465 for SMTP/SSL was NEVER an official (Per RFCs) Port for Mail…

My 2 cents
Andy