[MlMt] Timeout when setting up SSL/TLS.

[Han Trinh]

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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