Benny,

I just sent you my server logs from my work account that I’m having the issues with smtp.office365.com on port 587. The issue happens intermittently but very often. The only way I can recover is to keep retrying or by closing and restarting MailMate.


Note: setting smtp.office365.com to port 25 (with SSL) doesn’t work. I can’t send any emails through that setup. So had to switch it back to port 587.


I wonder if something happened recently with office 365’s SMTP servers, or perhaps a bug in an apple os update? Hopefully there is something we can do to help alleviate or fix this issue.



…Han


On 1 Dec 2016, at 22:20, Han Trinh wrote:

I’m been having the same issues as Simon on office 365.

Been using port 587 and will try switching to port 25 (with SSL) and report back after some milage. If it doesn’t work I’ll send some logs over as per Benny’s suggestion.

…Han

On 1 Dec 2016, at 20:53, Simon Kaplan wrote:

Hi Benny

Turns out I was using port 587 for office365 smtp (per their documentation). I changed to port 25 (with SSL) and the problem went away. If it occurs again then I’ll send the logs, but so far so good.

OTOH if you want logs of the problem, I’ll switch back to 587 and make them for you….

cheers
Simon
--
Simon Kaplan, co-founder & CEO
North Shore Labs Pty Ltd
ph: +61 411 511 122

On 1 Dec 2016, at 23:39, Benny Kjær Nielsen wrote:

On 30 Nov 2016, at 8:59, Simon Kaplan wrote:

Recently I started intermittently having the problem that when I send email from my office365 account using MailMate, I get this error:

Timeout when setting up SSL/TLS.

Retrying tends to send the message without any problems. I don’t recall having this problem with any of my google accounts.

If anyone has any suggestions for overcoming this, I’d be most grateful.

I'll need some logs to analyze the issue in more detail. Keep the Activity Viewer open (⌥⌘0) and when you have seen the issue once or twice then use “Help ▸ Send Server Logs”. Then I'll review them.

--
Benny
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