Gmail says "Messages missing a valid address in From:"

[Glenn Turner]

I have a issue sending to gmail accounts. Gmail says "Messages missing a valid address in From:"

On mail server 1.2.2.0

Anyone else had this issue

[DLVR 000006 20-12-19 22:45:54] Delivering item no 1276887, threads in use: 1

[DLVR 000006 20-12-19 22:45:54] Delivering item 1276887

[DLVR 000006 20-12-19 22:45:54] Resolving MX records for domain gmail.com.

[DLVR 000006 20-12-19 22:45:54] Retrieved 5 MX records for domain gmail.com

[DLVR 000006 20-12-19 22:45:54] Delivering mail to 1 recipient(s) at domain gmail.com using exchanger gmail-smtp-in.l.google.com.

[DLVR 000006 20-12-19 22:45:54] 220 mx.google.com ESMTP w20si9529132wmc.96 - gsmtp

[DLVR 000006 20-12-19 22:45:54] EHLO gyroscope.com

[DLVR 000006 20-12-19 22:45:54] 250-mx.google.com at your service, [77.68.14.172]

[DLVR 000006 20-12-19 22:45:54] 250-SIZE 157286400

[DLVR 000006 20-12-19 22:45:54] 250-8BITMIME

[DLVR 000006 20-12-19 22:45:54] 250-STARTTLS

[DLVR 000006 20-12-19 22:45:54] 250-ENHANCEDSTATUSCODES

[DLVR 000006 20-12-19 22:45:54] 250-PIPELINING

[DLVR 000006 20-12-19 22:45:54] 250-CHUNKING

[DLVR 000006 20-12-19 22:45:54] 250 SMTPUTF8

[DLVR 000006 20-12-19 22:45:54] STARTTLS

[DLVR 000006 20-12-19 22:45:54] 220 2.0.0 Ready to start TLS

[DLVR 000006 20-12-19 22:45:54] Switched to secure channel

[DLVR 000006 20-12-19 22:45:54] EHLO gyroscope.com

[DLVR 000006 20-12-19 22:45:54] 250-mx.google.com at your service, [77.68.14.172]

[DLVR 000006 20-12-19 22:45:54] 250-SIZE 157286400

[DLVR 000006 20-12-19 22:45:54] 250-8BITMIME

[DLVR 000006 20-12-19 22:45:54] 250-ENHANCEDSTATUSCODES

[DLVR 000006 20-12-19 22:45:54] 250-PIPELINING

[DLVR 000006 20-12-19 22:45:54] 250-CHUNKING

[DLVR 000006 20-12-19 22:45:54] 250 SMTPUTF8

[DLVR 000006 20-12-19 22:45:54] MAIL FROM:<HAVE REMOVED DUE TO POSTING IN FORUM> SIZE=2212

[DLVR 000006 20-12-19 22:45:54] 250 2.1.0 OK w20si9529132wmc.96 - gsmtp

[DLVR 000006 20-12-19 22:45:54] RCPT TO:<HAVE REMOVED DUE TO POSTING IN FORUM>

[DLVR 000006 20-12-19 22:45:55] 250 2.1.5 OK w20si9529132wmc.96 - gsmtp

[DLVR 000006 20-12-19 22:45:55] DATA

[DLVR 000006 20-12-19 22:45:55] 354  Go ahead w20si9529132wmc.96 - gsmtp

[DLVR 000006 20-12-19 22:45:55] Transmitted 2212 bytes plus CR.LF

[DLVR 000006 20-12-19 22:45:55] 550-5.7.1 [77.68.14.172      14] Messages missing a valid address in From:

[DLVR 000006 20-12-19 22:45:55] 550 5.7.1 header, or having no From: header, are not accepted. w20si9529132wmc.96 - gsmtp

[DLVR 000006 20-12-19 22:45:55] QUIT

[DLVR 000006 20-12-19 22:45:55] There was a problem using secure connection: 550 5.7.1 header, or having no From: header, are not accepted. w20si9529132wmc.96 - gsmtp.  Will attempt non-secure in 5 seconds.

[ArGoSoft Products]

You must have something there which alters FROM header.

It is definitely not from your server.

[Glenn Turner]

Ah sure enough anti-virus did an update and sure enough started checking email ports. Turned off.

Hopefully that sure fix it.

[ArGoSoft Products]

OK, I am almost sure it will fix it.

[Glenn Turner]

I'm still getting this occurring after many months. I've never been able to pin down the cause.

There is no anti-virus looking on pop/ smtp ports etc as far as I can tell.

I can send to gmail accounts. but sometimes when sending to the same gmail email address it says

550-5.7.1 [77.68.14.172      14] Messages missing a valid address in From:

The from address line appears that same with a successful or fail email.

Strangely the email client does appear to be key to things. Outlook appears to work fine to gmail accounts but IIS doesn't even though the to/from/subject/message is the same.

[Glenn Turner]

I did confirm it was client related and only with IIS email sends to gmail accounts.

I've changed the code and it now is working again. It must be something in the message that causes the error/bug to gmail accounts.

PROBABLY nothing to do with argosoft.