Problem migrating from POP3 server: no login attempt

Question asked by AWRData - 5/12/2025 at 5:30 PM

Answered

I am attempting to migrate a new user from a POP3 server which exists within my infrastructure. When I enter the necessary information into the migration, SM returns "Authentication with POP server failed" and the POP3 server logs indicate no attempt to log in, it just disconnects. I have tried both SSL on port 995, and unencrypted on port 110 with the same results.

I have tested the POP3 login manually to find it does work. I need to know in which SM logs to look to help determine the break-down, and maybe if anyone else has had issues with the POP3 migration.

9 Replies

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Linda Pagillo Replied

5/15/2025 at 10:02 AM

When connecting to the POP3 server, are you using the full email address of the user?

Linda Pagillo Mail's Best Friend Email: linda.pagillo@mailsbestfriend.com Web: www.mailsbestfriend.com Authorized SmarterTools Reseller Authorized Message Sniffer Reseller

Kyle Kerst Replied

5/15/2025 at 10:54 AM

Employee Post

It might help to get some detailed logging on this. You should be able to increase the POP Retrieval logging to Detailed within Manage>Troubleshooting>Options then reattempt the migration to see if any errors are generated in that log file. Those logs can be reviewed in Manage>Troubleshooting>View Logs.

Kyle Kerst Acting IT Manager SmarterTools Inc. www.smartertools.com

AWRData Replied

5/15/2025 at 1:33 PM

Thanks, Kyle, that is exactly what I was looking for. The problem is the old server is rejecting the CAPA command. Is there a way around this in SmarterMail?

Kyle Kerst Replied

5/15/2025 at 2:03 PM

Employee Post

You're very welcome. Does the result you see in the logs change depending on whether or not you use SSL/TLS? I wonder if the old server might be rejecting the CAPA attempt because its over an unsecured channel or something along those lines. I'm not sure of a way to bypass it, but I do know we had a CAPA-related fix included in our most recent release:

Fixed: IMAP sends untagged capability response after successful authentication instead of including it in the tagged OK response.

Worst case it might be worth upgrading to that to see if it has any impact on your results. If you're on an older build there may be additional release notes between then and now that influence your results as well.

Kyle Kerst Acting IT Manager SmarterTools Inc. www.smartertools.com

AWRData Replied

5/15/2025 at 3:07 PM

The old server is Post.Office (anyone remember that?) and it is secured via stunnel, so it has no clue of the difference between secure and insecure. As well, I bypassed the SSL and it still threw the same error.

Lastly, I am on the latest SmarterMail build.

AWRData Replied

5/15/2025 at 3:08 PM

Marked As Answer

I might just rig up an instance of mailutil to move from the old POP3 mailbox to SmarterMail via IMAP.

Kyle Kerst Replied

5/15/2025 at 3:20 PM

Employee Post

That might be a tricky one, and some sort of intermediary might be your best bet as you suggested. I can put in a discussion task to have this reviewed though in the meantime. Perhaps we can detect when CAPA is unsupported and continue the session without it, albeit under limited capability support.

Kyle Kerst Acting IT Manager SmarterTools Inc. www.smartertools.com

AWRData Replied

5/15/2025 at 6:01 PM

I was able to transfer the POP3 mailbox to SmarterMail via mailutil. Nothing like a powerful old Unix utility!

For my purposes, these are my last handful of customers to move off the old Post.Office server, so unsupported CAPA is no longer an issue for me. It could become an issue for others dealing with ridiculously old POP3 servers. Heck, even UW-IMAP's in.ipop3d supports CAPA.

Otherwise, this issue is resolved for me.

Kyle Kerst Replied

5/19/2025 at 5:00 PM

Employee Post

That is great to hear, glad to hear that did the trick! I've got this bookmarked so I can keep it on my radar. Thanks for your follow up on this!

Kyle Kerst Acting IT Manager SmarterTools Inc. www.smartertools.com

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