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send mail from command line using Gmail

Posted on 2016-09-05
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Last Modified: 2016-09-10
Hi

I can't despite my many efforst find a means to send an email from the command line on my Win2012r2 server

The idea is to use the Task Scheduler to send these but whatever utility I try ex. sendemail, switch-mail, mailsend
it just fails, here is the output from mailsend:

Winsock error[10060]: A connection attempt failed because the connected party di
d not properly respond after a period of time, or established connection failed
because connected host has failed to respond.

Error: Connection is closed unexpectedly
Could not send mail

this is my syntax:

mailsend.exe -t xxxxx@different.com -f xxxx@gmail.com -starttls -port 465 -auth -smtp smtp.gmail.com -sub test -M test -user xxxxxx@gmail.com -pass xxxxxxxxxxxxxxxxx

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I tried disabling the anti-virus: same result
Thunderbird which is on this computer communicates quite successfully with Gmail.

thanks
yann
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Question by:Yann Shukor
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by:Bing CISM / CISSP
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by:Tomas Valenta
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If you are using Google Apps you can do it by sending messages to
the server smtp-relay.gmail.com and by adding your public
IP address what will messages send to allowed hosts in Google Admin console.
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Expert Comment

by:Tomas Valenta
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If you have free Gmail account you need to enable IMAP/POP3 access to this mailbox
and add authentication in your script:
https://github.com/muquit/mailsend/blob/master/doc/examples.mediawiki#SSL__AUTHENTICATION
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Yann Shukor earned 0 total points
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Hi

I just realised my mistake

I have enabled two factor authentication on my Google account !

I will have to create a special purpose password for this to function !

thanks all the same

yann
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by:Yann Shukor
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