Build 7339 - Smartermail on Android Outlook

Problem reported by Jason Adams - 2/7/2020 at 9:10 AM

Resolved

Since we have updated to Build 7339 Smartermail on Android Outlook will not receive messages. I have deleted the account from my phone and now it cannot be added back, it tells me invalid email address and/or password. I have tried adding it three times with no joy. Anyone else experience this? Hopefully someone can tell me how to fix it.

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Sébastien Riccio Replied

2/9/2020 at 1:16 PM

For testing purpose I use it with EAS, but I will try with IMAP and give you some feedback.

Sébastien Riccio System & Network Admin https://swisscenter.com

echoDreamz Replied

2/9/2020 at 4:33 PM

I havent personally tested, but many of our users have reported this same issue. Most have moved on to the native client that ships with the phone.

Sébastien Riccio Replied

2/9/2020 at 10:39 PM

Hello,

I did some test on our beta testing environnement. First thing, Outlook Android using exchange mode (ActiveSync) still works on latest beta. That's at least a good thing.

Then I did a test configuring the account in Outlook Android as IMAP/SMTP and yes I can confirm it doesnt work.

The result is a popup screen saying I need to check the login/pass of my account.

I've looked through the IMAP logs and discovered something interresting:

[2020.02.10] 06:29:24.370 [52.125.139.145][48810908] connected at 10.02.2020 06:29:24
[2020.02.10] 06:29:24.464 [52.125.139.145][48810908] command: LCX0 CAPABILITY
[2020.02.10] 06:29:24.464 [52.125.139.145][48810908] response: * CAPABILITY IMAP4rev1 AUTH=CRAM-MD5 AUTH=NTLM AUTH=PLAIN UIDPLUS QUOTA XLIST CHILDREN ENABLE CONDSTORE IDLE
[2020.02.10] 06:29:24.464 [52.125.139.145][48810908] response: LCX0 OK CAPABILITY completed
[2020.02.10] 06:29:24.558 [52.125.139.145][48810908] command: LCX1 AUTHENTICATE NTLM
[2020.02.10] 06:29:24.730 [52.125.139.145][48810908] response: LCX1 BAD authentication failed NTLM Failure
[2020.02.10] 06:29:24.761 [52.125.139.145][48810908] disconnected at 10.02.2020 06:29:24
[2020.02.10] 06:29:54.823 [IP Unknown][62154796] Authentication failed because the remote party has closed the transport stream.

Everytime I try to add the account, there is a connexion from a microsoft owned IP addres that tries to login using NTLM but fails.

My guess here is that Outlook on Android to validate the account verifies it first through some tool on their infrastructure (why the f***?).

The verification is made with NTLM as it is announced by SmarterMail recent builds but it fails. (I triple checked the login/pass).

For SMTP I have nothing in the logs. Here I think that it first checks IMAP but as it fails it aborts and doesn't check SMTP at all.

Conclusion:

- There is maybe a global problem with NTLM on IMAP

- Or maybe only when negociating with microsoft client that wants to verify the account.

Sébastien Riccio System & Network Admin https://swisscenter.com

Sébastien Riccio Replied

2/9/2020 at 10:53 PM

My previous message was for IMAP attempt with port 993 (SSL) where the problem seems around NTLM.

For port 143 (with starttls) the issue is even different. Outlook on Android says the server certificate is not valid, but it is. You can tell it to ignore the error, but then the same popup comes back.

So I did an IMAP connectivity test for port 143 on https://testconnectivity.microsoft.com/ and here is the result:

And in the IMAP logs of the server:

2020.02.10] 06:41:38.511 [13.74.35.9][6591113] connected at 10.02.2020 06:41:38
[2020.02.10] 06:41:38.542 [13.74.35.9][6591113] command: 1 CAPABILITY
[2020.02.10] 06:41:38.542 [13.74.35.9][6591113] response: * CAPABILITY IMAP4rev1 AUTH=CRAM-MD5 AUTH=NTLM AUTH=PLAIN UIDPLUS QUOTA XLIST CHILDREN ENABLE CONDSTORE IDLE STARTTLS
[2020.02.10] 06:41:38.542 [13.74.35.9][6591113] response: 1 OK CAPABILITY completed
[2020.02.10] 06:41:38.573 [13.74.35.9][6591113] command: 2 STARTTLS
[2020.02.10] 06:41:38.651 [13.74.35.9][6591113] Could not negotiate TLS session: The remote host closed the connection.
[2020.02.10] 06:41:38.651 [13.74.35.9][6591113] disconnected at 10.02.2020 06:41:38

It fails to negotiate the TLS session and both microsot connectivity analyzer and the server seems to show this.

EDIT: I did a complemantary test from the microsoft connectivity analyzer but against another server we have (IMAP served by dovecot, port 143/starttls) using the same certificate as the one used on our SmarterMail test box (it's a star certificate *.domain.com) and all is successful:

I guess we're having two different problems here that makes Outlook on Android not usable with SmarterMail IMAP implementation .

Kind regards

Sébastien Riccio System & Network Admin https://swisscenter.com

Larry Duran Replied

2/10/2020 at 8:57 AM

Employee Post

Hey all, we're seeing similar issues as well with the Outlook app. I've added it to our bugs list for further investigation.

Larry Duran Software Developer SmarterTools Inc. www.smartertools.com

Shaun Peet Replied

2/10/2020 at 10:04 AM

My understanding of how Outlook for Android / iOS worked was that Microsoft was setting up the accounts in their cloud, and then the devices were connecting to the account in the cloud and not directly to the server. Perhaps that's changed now, but I thought they were doing that so the apps would always use "exchange" to connect from the device to the cloud, and then the cloud would connect to the mail servers using whatever other supported protocols existed.

Originally this was a security concern as there was third-party services in the mix, but now everything is run directly within Microsoft's realm - but I think the underlying methodology remains.

Sébastien Riccio Replied

2/16/2020 at 3:46 AM

I tested the issue again with latest build. IMAP/SMTP now works on outlook android.

However microsoft connectivity analyzer still shows the same "handshake failed" for IMAP with TLS on port 143.

Maybe it's specific to their analyzer but the same test works with another imap server (dovecot with same certificate)

Sébastien Riccio System & Network Admin https://swisscenter.com

Kyle Kerst Replied

2/20/2020 at 12:21 PM

Employee Post

Sebastien, good finds all around! Thanks for your efforts on this.

Kyle Kerst IT Coordinator SmarterTools Inc. www.smartertools.com

Nathan Replied

7/20/2020 at 1:08 PM

We still seem to be encountering this Outlook for Android issue (unable to connect using IMAP) with build 7482. Was this ever resolved, is anyone else still encountering it?

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