[Users] Authentication error

Libby Hughes libby_hughe5 at hotmail.com
Mon Aug 10 02:26:19 CEST 2015

When I try to send encrypted emails in Claws, the network log shows as below. This is with plain SMTP auth, port 587. But it is the same with login auth. I leave the user ID and password boxes blank with plain auth. Is this right? I would really be happy if someone could help me. i have been trying to send an encrypted email for 2 days and haven't managed it yet!
* Account 'emily_wil0 at hotmail.com@pop-mail.outlook.com': Connecting to SMTP server: smtp-mail.outlook.com:587...[01:07:24] SMTP< 220 BLU436-SMTP45.smtp.hotmail.com Microsoft ESMTP MAIL Service, Version: 8.0.9200.16384 ready at  Sun, 9 Aug 2015 17:07:23 -0700 [01:07:24] ESMTP> EHLO localhost[01:07:24] ESMTP< 250-BLU436-SMTP45.smtp.hotmail.com Hello [][01:07:24] ESMTP< 250-TURN[01:07:24] ESMTP< 250-SIZE 41943040[01:07:25] ESMTP< 250-ETRN[01:07:25] ESMTP< 250-PIPELINING[01:07:25] ESMTP< 250-DSN[01:07:25] ESMTP< 250-ENHANCEDSTATUSCODES[01:07:25] ESMTP< 250-8bitmime[01:07:25] ESMTP< 250-BINARYMIME[01:07:25] ESMTP< 250-CHUNKING[01:07:25] ESMTP< 250-VRFY[01:07:25] ESMTP< 250-TLS[01:07:25] ESMTP< 250-STARTTLS[01:07:25] ESMTP< 250 OK[01:07:25] ESMTP> STARTTLS[01:07:25] ESMTP< 220 2.0.0 SMTP server ready[01:07:26] ESMTP> EHLO localhost[01:07:26] ESMTP< 250-BLU436-SMTP45.smtp.hotmail.com Hello [][01:07:26] ESMTP< 250-TURN[01:07:26] ESMTP< 250-SIZE 41943040[01:07:26] ESMTP< 250-ETRN[01:07:26] ESMTP< 250-PIPELINING[01:07:26] ESMTP< 250-DSN[01:07:26] ESMTP< 250-ENHANCEDSTATUSCODES[01:07:26] ESMTP< 250-8bitmime[01:07:26] ESMTP< 250-BINARYMIME[01:07:26] ESMTP< 250-CHUNKING[01:07:26] ESMTP< 250-VRFY[01:07:26] ESMTP< 250-AUTH LOGIN PLAIN XOAUTH2[01:07:26] ESMTP< 250 OK[01:07:26] ESMTP> [AUTH PLAIN][01:07:26] ESMTP< 535 5.0.0 Authentication Failed** error occurred on authentication*** Authentication failed:535 5.0.0 Authentication Failed
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