smtp does not work on office365

[torstenwerner]

Heartbleed -service=smtp smtp.office365.com:587
2014/04/11 10:17:51 smtp.office365.com:587 - ERROR: Server does not support STARTTLS (503 5.5.2 Send hello first)

[lanrat]

This is because Microsoft does not support TLS for any of their SMTP servers.

[yakatz]

@lanrat This is not correct, but Microsoft SMTP does require EHLO first:

~ yehuda$ telnet smtp.office365.com 587
Trying 132.245.17.34...
Connected to outlook-nameast.office365.com.
Escape character is '^]'.
220 BLUPR02CA041.outlook.office365.com Microsoft ESMTP MAIL Service ready at Fri, 11 Apr 2014 21:10:09 +0000
STARTTLS
503 5.5.2 Send hello first
EHLO yehuda
250-BLUPR02CA041.outlook.office365.com Hello [184.199.189.146]
250-SIZE 78643200
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
250-STARTTLS
250-8BITMIME
250-BINARYMIME
250 CHUNKING

[yakatz]

Although I would be really surprised if Office 365 used OpenSSL instead of a Microsoft Crypto provider.
Configuring Exchange Server with TLS: http://support.microsoft.com/kb/829721

[lanrat]

@yakatz My bad, it is hotmail and outlook that don't support SMTP STARTTLS.