When trying to setup the custom SMTP server with the correct details, “Message could not be sent” error is shown when clicking to test email settings. I had previously been using an older version of Manager, and was unable to send emails using defaults or the custom SMTP and updated to the latest v…

Only port 587 (STARTTLS) is supported in Manager. 465 (SSL) won’t work. This might be weird test but could you try the following? First send an email when custom SMTP is disabled. Don’t close the program. After email when SMTP is disabled is successfully received. Set up custom SMTP (with port 587…

You’re right, that test would be weird :slight_smile:… but the result isn’t. Still displaying the “Message could not be sent” error. Tried twice for prosperity. I verified the email without custom SMTP is delivered. Also checked inbox/spam/trash for the email with custom SMTP, in case it was deli…

My initial guess was that there is something odd happening with root certification authorities. This would explain why plain SMTP works and SMTP over SSL doesn’t. But as you say, the same settings work fine on Windows machine, they don’t work on Mac OS X. Correct?

I’ve been having a play about with this all day, trying to hone in. That process is still ongoing. Manager on Windows handles whatever I throw at it. Plain SMTP works on both my Macs. I also had a volume with an older OSX on it (10.10.2), booted that up to test with a fresh install; same response …

This could be an issue with underlying SMTP implementation in Mono framework which Manager is using on Mac OS X. In that case there is nothing you can do to fix this. I will need to replace library Manager is using internally for SMTP connections.

I too am having this problem: I cannot set up an SSL SMTP server connection to send my emails. Is there a timeframe by when this could be fixed?

I managed to get it to work with port 587 and without the SSL option - but it is not clear to me whether any form of encryption is now being applied or not.

I can’t speak precisely to the cloud edition, as I use desktop edition. However, if it sends without SSL checked for port 587 then that mail server either does not require SSL on port 587, or just does not support it. You could test with Hotmail’s server “ smtp-mail.outlook.com ” on port 587 without…

[image] smi89: Between that and packet inspecting, I can see that the STARTTLS is being sent and received by the server. The server hello completes and then the TLS handshake fails for some reason. Could you try again in the latest version? If it still fails, then the issue must be in underly…

Issue remains in Manager Desktop 16.3.37. The TLS handshake still fails. Tested with Zoho and Hotmail on both my Macs. Out of curiosity, I’ve also tested in linux using Ubuntu 14.04/15.10 and the issue does not occur there. SSL SMTP happily connects, so this does seem more specific to Mono on OSX, …

Cannot email with custom SMTP on OS X

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For sending emails, custom SMTP now required	85	8969	July 24, 2019
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No luck with custom SMTP	4	1209	November 3, 2014

Cannot email with custom SMTP on OS X

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