Same exact thing here possibly. The strange thing about UC module vm pro 9.0.4 is that there is no TLS checkbox--though it still might be doing TLS anyway (see trace below). I can get it to work perfectly with office 365 through the IPO 500v2 (using alarms over SMTP) but the same settings don't seem to work for vm pro on the UCM.
Did you get it to work? Anyone know a way to send out through the IP Office 500v2 when using VM Pro? 127.0.0.1 or something? That would be great.
My trace is below--it says authentication error but I've checked and compared settings again and again with the one that works though the 500v2 (on 9.0.4). This one also used port 25 but I get the same error with port 587
/2014 14:43:31.968 - Attempting to connect to host smtp.office365.com on port 25, local bound address is (null)
04/12/2014 14:43:32.128 - Successfully connected to host smtp.office365.com on port 25
04/12/2014 14:43:32.193 - < 220 CY1PR09XXXX33.outlook.office365.com Microsoft ESMTP MAIL Service ready at Thu, 4 Dec 2014 22:43:36 +0000
04/12/2014 14:43:32.255 - ######## START OF CHUNK ######
04/12/2014 14:43:32.324 - > EHLO uc-module
04/12/2014 14:43:32.443 - ######## END OF CHUNK ######
04/12/2014 14:43:32.562 - < 250-CY1PR09CA0033.outlook.office365.com Hello [50.254.xxx.xxx]
04/12/2014 14:43:32.562 - 250-SIZE 78643200
04/12/2014 14:43:32.562 - 250-PIPELINING
04/12/2014 14:43:32.562 - 250-DSN
04/12/2014 14:43:32.562 - 250-ENHANCEDSTATUSCODES
04/12/2014 14:43:32.562 - 250-STARTTLS
04/12/2014 14:43:32.562 - 250-8BITMIME
04/12/2014 14:43:32.562 - 250-BINARYMIME
04/12/2014 14:43:32.562 - 250 CHUNKING
04/12/2014 14:43:32.679 - ######## START OF CHUNK ######
04/12/2014 14:43:32.739 - > STARTTLS
04/12/2014 14:43:32.801 - ######## END OF CHUNK ######
04/12/2014 14:43:32.911 - < 220 2.0.0 SMTP server ready
04/12/2014 14:43:33.130 - ######## START OF CHUNK ######
04/12/2014 14:43:33.246 - > EHLO uc-module
04/12/2014 14:43:33.309 - ######## END OF CHUNK ######
04/12/2014 14:43:33.440 - < 250-CY1PRXXXX0033.outlook.office365.com Hello [50.254.xxx.xxx]
04/12/2014 14:43:33.440 - 250-SIZE 78643200
04/12/2014 14:43:33.440 - 250-PIPELINING
04/12/2014 14:43:33.440 - 250-DSN
04/12/2014 14:43:33.440 - 250-ENHANCEDSTATUSCODES
04/12/2014 14:43:33.440 - 250-AUTH LOGIN
04/12/2014 14:43:33.440 - 250-8BITMIME
04/12/2014 14:43:33.440 - 250-BINARYMIME
04/12/2014 14:43:33.440 - 250 CHUNKING
04/12/2014 14:43:33.506 - ######## START OF CHUNK ######
04/12/2014 14:43:33.616 - > AUTH LOGIN
04/12/2014 14:43:33.677 - ######## END OF CHUNK ######
04/12/2014 14:43:33.736 - < 334 VXNlcmxxxbWU6
04/12/2014 14:43:33.847 - ######## START OF CHUNK ######
04/12/2014 14:43:33.963 - > YXZheWEtdm1AYWxxxxGFzY3xxxHRyeC5jb20=
04/12/2014 14:43:34.088 - ######## END OF CHUNK ######
04/12/2014 14:43:34.200 - < 334 UGFzc3dvcmQ6
04/12/2014 14:43:34.320 - ######## START OF CHUNK ######
04/12/2014 14:43:34.382 - > QWxwaxxxMjM=
04/12/2014 14:43:34.499 - ######## END OF CHUNK ######
04/12/2014 14:43:39.918 - < 535 5.7.3 Authentication unsuccessful
04/12/2014 14:43:40.034 - bool CSMTPConnection::AuthLogin(SQLUINTEGER&, const TCHAR*, const TCHAR*): AUTH LOGIN authentication was unsuccessful
04/12/2014 14:43:40.147 - ######## START OF CHUNK ######
04/12/2014 14:43:40.209 - > QUIT