Can't find error in logs

Question asked by Mark Thornton - 10/22/2024 at 1:11 PM

Unanswered

I had a Outlook Desktop client with a stuck outbox. Email was still coming in, but nothing going out. The error message in the client was "We can't complete because we can't contact the server right now, please try again." I've looked through the logs searching on the user name and haven't found anything that jumps out as a problem. Where would outbox sending errors from Outlook desktop wind up?

4 Replies

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Tony Scholz Replied

10/22/2024 at 1:18 PM

Employee Post

Hello Mark,

You will want to look on the machine for this issue as the connection to the mail server was never made. With no connection nothin will be in the SmarterMail logs.

Things that can be tested on why the server was unreachable.

can the server be pinged
can a telnet to the correct port be made with a 200 response
1. openssl for secure connections ( 465, 25/587 with STARTTLS )
anything in Outlooks advanced logging?

For these tests to work they will need to be performed during the issue from the clients machine.

Other possible options as well.

flush dns on the local machine
try starting outlook in safe mode.
check traffic on your firewall

Tony Scholz Lead Network/System Administrator SmarterTools Inc. www.smartertools.com

Mark Thornton Replied

10/22/2024 at 2:34 PM

I'm going to look this evening and see if I find anything in the logs on the client. The confusing part is the client was contacting the server and downloading new email. The user started deleting the messages in the outbox and then all of it went out. I have asked the user to not empty their deleted emails so I can find the offending message.

Eric G Replied

2/13/2025 at 9:23 AM

We are dealing with this exact issue and it is affecting a single client on both his desktop and laptop. No other users are experiencing this problem.

The client happens to have 56 folders under the Inbox (which is of course a big no-no), which we’ve advised against in the past, though it had been working fine until about a month ago.

Given that the issue persists across multiple devices and only affects this client, has anyone identified the cause or found any further clues? Any insights would be greatly appreciated!

Kyle Kerst Replied

2/13/2025 at 10:51 AM

Employee Post

I have seen behaviors like this in the past with corrupt messages in the outbox. Once one gets in there anything behind it will fail to go out as well, so once they delete the offending message the rest tend to go out without further trouble. Is there anything special about the message they deleted that got things moving again? I'd be on the lookout for attachments, signatures or signature images, etc. If you can narrow that down it can make troubleshooting the issue significantly easier.

Kyle Kerst Lead Internal Network/System Administrator SmarterTools Inc. smartertools.com

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