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I used to be able to send files using:

mpack -subject <somefile> me@example.com 

but now I'm getting the following message:

sendmail: Cannot open smtp.gmail.com:587

My /etc/ssmtp/ssmtp.conf containts the following:

root=postmaster
mailhub=smtp.gmail.com:587
hostname=myhost
AuthUser=myemail@gmail.com
AuthPass=mypassword
FromLineOverride=YES
UseSTARTTLS=YES

I checked my gmail account, and Allow less secure apps is set to ON

Any ideas on how to troubleshoot this?

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    Analyzing the actual traffic between your system and the Gmail server(s) might give you more info. The error you see on the screen is just the text sendmail displays when whatever this condition occurs. I would use tcpdump or wireshark on your system, capture the traffic while you try to send the file, then review the session information to see what specifically is failing in the exchange. Hope this helps! – 0xSheepdog Feb 2 '18 at 18:08
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    turns out my dns isn't resolving properly. – WhiskerBiscuit Feb 2 '18 at 19:08
  • Hey, that's progress. Good to know. You should consider posting an answer to your own question, explaining how you determined the problem and how it was resolved. – 0xSheepdog Feb 2 '18 at 19:12

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