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<p dir="auto">Benny,</p>
<p dir="auto">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.</p>
<p dir="auto">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.</p>
<p dir="auto">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.</p>
<p dir="auto">…Han</p>
<p dir="auto">On 1 Dec 2016, at 22:20, Han Trinh wrote:</p>
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<p dir="auto">I’m been having the same issues as Simon on office 365.</p>
<p dir="auto">Been using port 587 and will try switching to port 25 (with SSL) and report back after some milage.<br>
If it doesn’t work I’ll send some logs over as per Benny’s suggestion.</p>
<p dir="auto">…Han</p>
<p dir="auto">On 1 Dec 2016, at 20:53, Simon Kaplan wrote:</p>
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<p dir="auto">Hi Benny</p>
<p dir="auto">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.</p>
<p dir="auto">OTOH if you want logs of the problem, I’ll switch back to 587 and make them for you….</p>
<p dir="auto">cheers</p>
<h2 style="font-size:1.2em">Simon</h2>
<p dir="auto">Simon Kaplan, co-founder & CEO<br>
North Shore Labs Pty Ltd<br>
ph: +61 411 511 122</p>
<p dir="auto">On 1 Dec 2016, at 23:39, Benny Kjær Nielsen wrote:</p>
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<p dir="auto">On 30 Nov 2016, at 8:59, Simon Kaplan wrote:</p>
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<p dir="auto">Recently I started intermittently having the problem that when I send email from my office365 account using MailMate, I get this error:</p>
<p dir="auto">Timeout when setting up SSL/TLS.</p>
<p dir="auto">Retrying tends to send the message without any problems. I don’t recall having this problem with any of my google accounts.</p>
<p dir="auto">If anyone has any suggestions for overcoming this, I’d be most grateful.</p>
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<p dir="auto">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.</p>
<p dir="auto">-- <br>
Benny</p>
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