SUMMARY Sending messages via smtp is not working. Upon debugging it, I see ksmtp never even tries to authenticate, and I'm not sure why. I enabled debugging for ksmtp, and set a log path. The log reads like this: S: 220 MRXP264CA0009.outlook.office365.com Microsoft ESMTP MAIL Service ready at Tue, 2 Jul 2019 12:57:33 +0000 C: EHLO hamra S: 250-MRXP264CA0009.outlook.office365.com Hello [212.98.155.122] S: 250-SIZE 157286400 S: 250-PIPELINING S: 250-DSN S: 250-ENHANCEDSTATUSCODES S: 250-STARTTLS S: 250-8BITMIME S: 250-BINARYMIME S: 250-CHUNKING S: 250 SMTPUTF8 C: STARTTLS S: 220 2.0.0 SMTP server ready C: EHLO hamra S: 250-MRXP264CA0009.outlook.office365.com Hello [212.98.155.122] S: 250-SIZE 157286400 S: 250-PIPELINING S: 250-DSN S: 250-ENHANCEDSTATUSCODES S: 250-AUTH LOGIN XOAUTH2 S: 250-8BITMIME S: 250-BINARYMIME S: 250-CHUNKING S: 250 SMTPUTF8 And just stops at this point, when one would expect it to proceed with "auth login". It stays like that until it times out, and tells me that sending failed. SOFTWARE/OS VERSIONS Linux/KDE Plasma: 5.1.10, KDE apps 19.04.1 (available in About System) KDE Plasma Version: KDE Frameworks Version: Qt Version: 5.12.3 ADDITIONAL INFORMATION