Closed
Description
Symfony version(s) affected
6.4.2
Description
This issue is similar to what is described on #49701.
When connecting to smtp-mail.outlook.com using STARTTLS and XOAUTH2, it attempts to first authenticate using LOGIN and then XOAUTH2. More often than not, the LOGIN authenticator times out at AbstractStream.php#L84. That exception is caught at EsmtpTransport.php#L202 and triggers a RSET. The timeout only occurs client side and the server later replies, but that difference causes the expected response $codes to get all confused.
How to reproduce
Connect to smtp-mail.outlook.com using starttls, an xoauth2 access token, and a timeout of 15s.
Possible Solution
- Increase
SocketStreamtimeout to a higher value to prevent the client side socket from timing out but that is arbitrary and doesn't fully solve the problem. - A client side connection timeout should terminate the connection rather than continue
Additional Context
Failed to authenticate on SMTP server with username "...." using the following authenticators: "LOGIN", "XOAUTH2". Authenticator "LOGIN" returned "Connection to "smtp-mail.outlook.com:587" timed out.". Authenticator "XOAUTH2" returned "Expected response code "235" but got code "250", with message "250 2.0.0 Resetting".".
[02:31:28] < 220 LO4P123CA0281.outlook.office365.com Microsoft ESMTP MAIL Service ready at Fri, 26 Jan 2024 14:31:28 +0000 [02:31:28] > EHLO [127.0.0.1] [02:31:29] < 250-LO4P123CA0281.outlook.office365.com Hello [35.176.196.6] [02:31:29] < 250-SIZE 157286400 [02:31:29] < 250-PIPELINING [02:31:29] < 250-DSN [02:31:29] < 250-ENHANCEDSTATUSCODES [02:31:29] < 250-STARTTLS [02:31:29] < 250-8BITMIME [02:31:29] < 250-BINARYMIME [02:31:29] < 250-CHUNKING [02:31:29] < 250 SMTPUTF8 [02:31:29] > STARTTLS [02:31:29] < 220 2.0.0 SMTP server ready [02:31:29] > EHLO [127.0.0.1] [02:31:29] < 250-LO4P123CA0281.outlook.office365.com Hello [35.176.196.6] [02:31:29] < 250-SIZE 157286400 [02:31:29] < 250-PIPELINING [02:31:29] < 250-DSN [02:31:29] < 250-ENHANCEDSTATUSCODES [02:31:29] < 250-AUTH LOGIN XOAUTH2 [02:31:29] < 250-8BITMIME [02:31:29] < 250-BINARYMIME [02:31:29] < 250-CHUNKING [02:31:29] < 250 SMTPUTF8 [02:31:29] > AUTH LOGIN [02:31:29] < 334 VXNlcm5hbWU6 [02:31:29] > [...username...] [02:31:29] < 334 UGFzc3dvcmQ6 [02:31:29] > [...passwd...] [02:31:44] > RSET /// Connection to "smtp-mail.outlook.com:587" timed out. (\Symfony\Component\Mailer\Exception\TransportException) [02:31:53] < 535 5.7.139 Authentication unsuccessful, the request did not meet the criteria to be authenticated successfully. Contact your administrator. [LO4P123CA0281.GBRP123.PROD.OUTLOOK.COM 2024-01-26T14:31:53.416Z 08DC1E4B43912AF4] [02:31:53] > AUTH XOAUTH2 [...access_token...] [02:31:58] < 250 2.0.0 Resetting [02:31:58] > RSET [02:31:59] < 235 2.7.0 Authentication successful