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I've been using Thunderbird for a while now and for some reason, when trying to send emails via Thunderbird in a Outlook/Hotmail account, this error message is displayed: "Login to server smtp.live.com failed.".

I've checked online and the smtp server settings seems to be correct:

  • Server name: smtp.live.com
  • Port: 587
  • Authentication: Normal password
  • Security: STARTTLS

I can receive emails on Outlook/Hotmail accounts, but I am unable to send emails on these same accounts. Any ideas?

Thank you for your support

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  • Try enabling SSL/TLS directly instead of using STARTTLS – nKn Sep 2 '15 at 12:30
  • It didn't work, the same error is displayed. Thank you for your help though :) – Kiqito Sep 3 '15 at 0:19
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I had a similar issue caused by (I think) too many characters in my password (though why it affected my SMTP logon but not POP3 I have no idea). Try logging in to your hotmail thru login.live.com and resetting to a password no more than 16 characters. edit: I can't tell you if Thunderbird (or Hotmail) changed the way it truncates passwords that may be too long. It's also possible either program parsed lengthy passwords with many special characters differently than in the past. A password that worked for months (and still worked to receive mail) suddenly (within the last few weeks) stopped working (for SMTP). Picking a simpler password did fix my problem but I'd be interested if anyone can definitively tell me what the problem was.

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