Big Sur smtpclient.apple connection to smtp.gmail.com reports failure on Mail Connection Doctor
The Mail Connection Doctor reports "Trying to log into SMTP account failed." Review of the log (below) suggests the "501 5.5.2 Cannot Decode response" is caused by the * (unexpected) cancel(?) issued at 12:04:23.704 which I assume leads to the failure status!
Is the "Check Again" simply trying to end the session because there is no actual email to be sent?
Curiously other (postfix) servers I connect to do not use the same command sequence and this doesn't seem to impede sending outbound emails via gmail.
Is there a configuration setting that I might be missing? Cheers, Frank.
-----------------------------------------------------------------------
INITIATING CONNECTION Jan 04 12:04:21.876 host:smtp.gmail.com -- port:587 -- socket:0x0 -- thread:0x6000052b1040
CONNECTED Jan 04 12:04:21.991 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:587 -- socket:0x60000629dc20 -- thread:0x6000052b1040
READ Jan 04 12:04:22.286 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:587 -- socket:0x60000629dc20 -- thread:0x6000052b1040
220 smtp.gmail.com ESMTP a15-20020a63e84f000000b0043b565cb57csm19136637pgk.73 - gsmtp
WROTE Jan 04 12:04:22.286 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:587 -- socket:0x60000629dc20 -- thread:0x6000052b1040
EHLO smtpclient.apple
READ Jan 04 12:04:22.562 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:587 -- socket:0x60000629dc20 -- thread:0x6000052b1040
250-smtp.gmail.com at your service, [123.208.20.153]
250-SIZE 35882577
250-8BITMIME
250-STARTTLS
250-ENHANCEDSTATUSCODES
250-PIPELINING
250-CHUNKING
250 SMTPUTF8
WROTE Jan 04 12:04:22.562 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:587 -- socket:0x60000629dc20 -- thread:0x6000052b1040
STARTTLS
READ Jan 04 12:04:22.829 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:587 -- socket:0x60000629dc20 -- thread:0x6000052b1040
220 2.0.0 Ready to start TLS
WROTE Jan 04 12:04:23.168 [kCFStreamSocketSecurityLevelTLSv1_2] -- host:smtp.gmail.com -- port:587 -- socket:0x60000629dc20 -- thread:0x6000052b1040
EHLO smtpclient.apple
READ Jan 04 12:04:23.435 [kCFStreamSocketSecurityLevelTLSv1_2] -- host:smtp.gmail.com -- port:587 -- socket:0x60000629dc20 -- thread:0x6000052b1040
250-smtp.gmail.com at your service, [123.208.20.153]
250-SIZE 35882577
250-8BITMIME
250-AUTH LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN OAUTHBEARER XOAUTH
250-ENHANCEDSTATUSCODES
250-PIPELINING
250-CHUNKING
250 SMTPUTF8
WROTE Jan 04 12:04:23.436 [kCFStreamSocketSecurityLevelTLSv1_2] -- host:smtp.gmail.com -- port:587 -- socket:0x60000629dc20 -- thread:0x6000052b1040
AUTH LOGIN
READ Jan 04 12:04:23.704 [kCFStreamSocketSecurityLevelTLSv1_2] -- host:smtp.gmail.com -- port:587 -- socket:0x60000629dc20 -- thread:0x6000052b1040
334 VXxxxxxxxxU6
WROTE Jan 04 12:04:23.704 [kCFStreamSocketSecurityLevelTLSv1_2] -- host:smtp.gmail.com -- port:587 -- socket:0x60000629dc20 -- thread:0x6000052b1040
*
READ Jan 04 12:04:23.974 [kCFStreamSocketSecurityLevelTLSv1_2] -- host:smtp.gmail.com -- port:587 -- socket:0x60000629dc20 -- thread:0x6000052b1040
501 5.5.2 Cannot Decode response a15-20020a63e84f000000b0043b565cb57csm19136637pgk.73 - gsmtp
WROTE Jan 04 12:04:23.974 [kCFStreamSocketSecurityLevelTLSv1_2] -- host:smtp.gmail.com -- port:587 -- socket:0x60000629dc20 -- thread:0x6000052b1040
AUTH LOGIN
READ Jan 04 12:04:24.247 [kCFStreamSocketSecurityLevelTLSv1_2] -- host:smtp.gmail.com -- port:587 -- socket:0x60000629dc20 -- thread:0x6000052b1040
334 VXxxxxxxxxU6
WROTE Jan 04 12:04:24.247 [kCFStreamSocketSecurityLevelTLSv1_2] -- host:smtp.gmail.com -- port:587 -- socket:0x60000629dc20 -- thread:0x6000052b1040
*
READ Jan 04 12:04:24.519 [kCFStreamSocketSecurityLevelTLSv1_2] -- host:smtp.gmail.com -- port:587 -- socket:0x60000629dc20 -- thread:0x6000052b1040
501 5.5.2 Cannot Decode response a15-20020a63e84f000000b0043b565cb57csm19136637pgk.73 - gsmtp
WROTE Jan 04 12:04:24.519 [kCFStreamSocketSecurityLevelTLSv1_2] -- host:smtp.gmail.com -- port:587 -- socket:0x60000629dc20 -- thread:0x6000052b1040
QUIT
MacBook Pro 15″, macOS 11.7