Outlook fails to connect with IMAP

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Outlook fails to connect with IMAP

Postby mollcons » Thu Mar 26th, 2015 2:37pm

Mailtraq Version: 2.17.7.3560

This may be a further enhancement to my previous problem with being unable to connect from Outlook 2013 (Office365) to Mailtraq using the standard connection criteria. Until Tuesday my Outlook client was connecting with Mailtraq just fine, both receiving and sending. On Tuesday Mailtraq got blocked up with mails in its pending folder (which I have now cleared), but at the same time, Outlook ceased to be able to connect to Mailtraq. I upgraded Mailtraq yesterday and this has not fixed the issue.

My Mailtraq instance is running on Windows 2012R2.
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Re: Outlook fails to connect with IMAP

Postby Malc » Thu Mar 26th, 2015 6:41pm

What entries are in Mailtraq's logs at that time? Are you able to telnet to Mailtraq on the same port as Outlook is trying to use? (It could be that the PC itself is firewalling connection attempts.)

I've found that, on my lovely wife's Macs, Secure IMAP became broken by a recent update to Avast!. Have you checked the Anti-Virus software on the Outlook PC?
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Re: Outlook fails to connect with IMAP

Postby mollcons » Thu Mar 26th, 2015 7:39pm

Yes. Checked and there has been no change so far as I can make out.
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Re: Outlook fails to connect with IMAP

Postby Malc » Mon Mar 30th, 2015 3:20am

To clarify, Chris, have you tried connecting with the Outlook client PC's anti-virus's mail-scanning facility disabled?
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Re: Outlook fails to connect with IMAP

Postby mollcons » Mon Apr 06th, 2015 4:30pm

Apologies for the delay, but I have been re-organising my study office.

In answer to your comment, my AV software (BitDefender) does not do any scanning of emails. That is done exclusively by Mailtraq for its email service. Outlook manages to collect and deliver email to other IMAP servers, but not to Mailtraq. My wife's PC collects and delivers email to/from Mailtraq using POP3 without problem.
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Re: Outlook fails to connect with IMAP

Postby mollcons » Fri Apr 24th, 2015 2:10pm

... and now I can no longer connect to Mailtraq with my Samsung Galaxy S5. It complains that (despite having NO changes to its configuration for over six months) that it cannot safely connect to server.

What has changed in Mailtraq? The only thing that has changed on my Samsung S5 is that I upgraded to Android 5 earlier this week. On my laptop which runs Windows 8.1 Update 1 and Office 365, nothing has changed in that configuration for many months, yet I am unable to connect now with either Outlook 365 or now my Samsung S5.

And I have only just renewed my Mailtraq licence (Grrrh!)....
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Re: Outlook fails to connect with IMAP

Postby mollcons » Wed May 06th, 2015 12:04pm

Any suggestions anyone?
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Re: Outlook fails to connect with IMAP

Postby Martin Clayton » Wed May 06th, 2015 1:15pm

Do the Mailtraq logs show anything interesting for the failed connections? And how about client-side; just guessing but the clients' security policies may have changed with various updates. Outlook points at a fairly generic security problem but does the Samsung say anything specific?

Also, how are you configured: e.g: imaps:993 & smtp:465 with Mtq in ssl implicit mode? What authentication method do the clients use? Is the certificate self-signed, does the host name you're using match the certificate Common Name... ? To test tls support you could try sending yourself an email from checktls pointing to a suitably enabled smtp service on Mailtraq.
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Re: Outlook fails to connect with IMAP

Postby mollcons » Mon May 11th, 2015 6:15am

So far as the attempted connection from Outlook, see attached error for the client end.

The Mailtraq log shows only this:
+ 0000217C 192.168.1.10 [11/05/2015 11:02]
00001000 00000C58 11/05/2015 11:02:35 IMAP: (Accept) Receiving connection from 192.168.1.10
00040000 0000217C 11/05/2015 11:02:35 192.168.1.10 is disconnecting
- 0000217C

So far as the Samsung S5 phone is concerned, the phone now tells me when trying to connect:
"Unable to set up account
Cannot safely connect to server"

I think the Mailtraq log that is relevant is:
+ 00002186 82.69.62.210 [11/05/2015 11:09]
00001000 00001AF0 11/05/2015 11:09:00 IMAP: (Accept) Receiving connection from 82.69.62.210
00040000 00002186 11/05/2015 11:09:00 82.69.62.210 is disconnecting
00040000 0000201F 11/05/2015 11:09:01 1YJW IDLE ---> 1YJW OK IDLE completed (131859ms)
00040000 0000201F 11/05/2015 11:09:02 GVCV SELECT "INBOX" ---> GVCV OK [READ-WRITE] SELECT completed (16ms)
00040000 0000201F 11/05/2015 11:09:02 4T8H UID SEARCH SINCE 11-Apr-2015 ---> 4T8H OK SEARCH completed (47ms)
- 00002186

On both devices I am connecting on ports 994 and 465. So far as the Samsung is concerned, when it was running Android 4 it connected fine, but ever since upgrading to Android 5, it has refused to connect.
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Re: Outlook fails to connect with IMAP

Postby mollcons » Mon May 11th, 2015 6:33pm

Interestingly, Outlook on Android actually connects successfully to Mailtraq (on my Samsung S5).
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Re: Outlook fails to connect with IMAP

Postby Martin Clayton » Tue May 12th, 2015 10:04am

mollcons wrote:Interestingly, Outlook on Android actually connects successfully

That could also point at google's security policy getting tighter. If that's the case, and given the lack of information in the log snippets, the client's view of what's happening is especially useful. I've managed to avoid android to-date but a quick search suggests that detailed debugging information is up for grabs. What we really want to see is something specific; authentication/encryption method not supported, tls protocol or cyphers suck, incomplete chain/intermediary not found, etc.

We're still in the dark but eventual resolution might require:

  • Client configuration change (new account auto-configuration might not help)
  • Set SslStrong=1 on the relevant Mailtraq services
  • Use a full-chain certificate that Mailtraq supports
  • Upgrade Mailtraq (the 3562 beta may be of interest)
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Re: Outlook fails to connect with IMAP

Postby mollcons » Wed May 13th, 2015 9:09am

I have updated to 3562.

There are no changes to either Outlook Windows, or Samsung Mail. Neither can connect any better.

The cert I am using is a self-signed certificate generate on Jan 1st 2015, and this works flawlessly with Thunderbird on Windows and also Outlook on Android.

I could not see how to configure SslStrong in the Mailtraq service properties (for any relevant service).
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Re: Outlook fails to connect with IMAP

Postby Martin Clayton » Thu May 14th, 2015 7:00am

mollcons wrote:There are no changes to either Outlook Windows, or Samsung Mail. Neither can connect any better.

It's always going to be slightly hit and hope unless we know your exact configuration and, in particular, the client view.

The cert I am using is a self-signed certificate generate on Jan 1st 2015, and this works flawlessly with Thunderbird on Windows and also Outlook on Android.

Thunderbird, at least, must have required a security exception for this to work. I've no idea about Outlook on Android's security policy. Most of what you've posted points to a client security issue which you may or may not be able to override client-side. It could be down to the untrusted tls chain, the host name not matching the certificate Common Name or something more technical...

I could not see how to configure SslStrong in the Mailtraq service properties (for any relevant service).

This requires manual editing of system.cfg See the note at http://info.mailtraq.com/certificate-manager

If that's no help, I'd focus on getting the clients to say what they don't like. I suspect that's easier with the android client.
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