swaks -t [email protected]

swaks -t [email protected] -s smtp.gmail.com:587 -tls -a LOGIN
.../...

=== Trying smtp.gmail.com:587...
=== Connected to smtp.gmail.com.
<-  220 smtp.gmail.com ESMTP 41be03b00d2f7-7f8c1c3224asm7641858a12.29 - gsmtp
 -> EHLO users-macbook-pro-2.local
<-  250-smtp.gmail.com at your service, [203.172.74.6]
<-  250-SIZE 35882577
<-  250-8BITMIME
<-  250-STARTTLS
<-  250-ENHANCEDSTATUSCODES
<-  250-PIPELINING
<-  250-CHUNKING
<-  250 SMTPUTF8
 -> STARTTLS
<-  220 2.0.0 Ready to start TLS
=== TLS started with cipher TLSv1.3:AEAD-CHACHA20-POLY1305-SHA256:256
=== TLS client certificate not requested and not sent
=== TLS no client certificate set
=== TLS peer[0]   subject=[/CN=smtp.gmail.com]
===               commonName=[smtp.gmail.com], subjectAltName=[DNS:smtp.gmail.com] notAfter=[2025-01-13T08:37:55Z]
=== TLS peer[1]   subject=[/C=US/O=Google Trust Services/CN=WR2]
===               commonName=[WR2], subjectAltName=[] notAfter=[2029-02-20T14:00:00Z]
=== TLS peer[2]   subject=[/C=US/O=Google Trust Services LLC/CN=GTS Root R1]
===               commonName=[GTS Root R1], subjectAltName=[] notAfter=[2028-01-28T00:00:42Z]
=== TLS peer certificate passed CA verification, passed host verification (using host smtp.gmail.com to verify)
 ~> EHLO users-macbook-pro-2.local
<~  250-smtp.gmail.com at your service, [203.172.74.6]
<~  250-SIZE 35882577
<~  250-8BITMIME
<~  250-AUTH LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN OAUTHBEARER XOAUTH
<~  250-ENHANCEDSTATUSCODES
<~  250-PIPELINING
<~  250-CHUNKING

<~  250 SMTPUTF8
 ~> AUTH LOGIN
<~  334 VXNlcm5hbWU6
 ~> c2F0aXMuaG91c2UuNjVAZ21haWwuY29t
<~  334 UGFzc3dvcmQ6
~> UmFxdWVsJk1hcnRpbjIwMjMh
<~* 534-5.7.9 Application-specific password required. For more information, go to
<~* 534 5.7.9  https://support.google.com/mail/?p=InvalidSecondFactor 41be03b00d2f7-7f8c1c3224asm7641858a12.29 - gsmtp
*** No authentication type succeeded
 ~> QUIT
<~  221 2.0.0 closing connection 41be03b00d2f7-7f8c1c3224asm7641858a12.29 - gsmtp
=== Connection closed with remote host.

Swaks, check_nuki.sh