PhpMailer not delivering emails.

Sup folks,

This is a weird one. I'm using roundcube as my primary emailer client and it works great.
I get the following in my logs when I compose a message to a gmail account. The message gets delivered.

Code:

2024-08-30T15:23:00.210987-03:00 www spamd[3019]: spamd: result: . -101 - ALL_TRUSTED,DKIM_SIGNED,DKIM_VALID,DKIM_VALID_AU,USER_IN_WELCOMELIST scantime=0.2,size=1473,user=spamd,uid=1001,required_score=5.0,rhost=localhost,raddr=::1,rport=41452,mid=<[email protected]>,autolearn=ham autolearn_force=no
2024-08-30T15:23:00.226617-03:00 www postfix/pipe[55903]: E1A7E7223C: to=<[email protected]>, relay=spamassassin, delay=0.32, delays=0.08/0.01/0/0.23, dsn=2.0.0, status=sent (delivered via spamassassin service)

For a mailing list I am using PHPMailer, I get the same log entries but the message is not delivered.
The only diffeence I can see is HTML_MESSAGE & TVD_SPACE_RATIO

Code:

2024-08-30T15:28:48.514291-03:00 www spamd[3019]: spamd: result: . -101 - ALL_TRUSTED,DKIM_SIGNED,DKIM_VALID,DKIM_VALID_AU,HTML_MESSAGE,TVD_SPACE_RATIO,USER_IN_WELCOMELIST scantime=0.1,size=1779,user=spamd,uid=1001,required_score=5.0,rhost=localhost,raddr=::1,rport=32952,mid=<[email protected]>,autolearn=ham autolearn_force=no
2024-08-30T15:28:48.539114-03:00 www postfix/pipe[57143]: 58FD572278: to=<[email protected]>, relay=spamassassin, delay=0.2, delays=0.08/0/0/0.13, dsn=2.0.0, status=sent (delivered via spamassassin service)

Any ideas as to why only the first one would be delivered?

 

Sure. Thanks.