Reply-to addres is faulty.

Question

Hi all,
I can't seem to find this problem anywhere else, sorry if this error has already been discussed elsewhere.
I'm using mail, and am running 3 accounts off it (two for work, one private). The last few weeks all of a sudden, all replies to my private e-mail are sent to my work account.
I can't seem to find where I can set the default 'reply to' address in Mail & I don't want to have to manually fill in the (correct) private address each time I send an e-mail from that account.
Is this a know bug & is there a way to 'reset' the default reply-to addresses?

Answer 1

You could try deleting (temporarily) the work smtp server listing from Mail Prefs (pick an account, edit smtp server, and delete work smtp server). Just remember to write down all the smtp server name and port number before you delete it, so you can put it back later. Then reboot, then try sending an email from the home account to yourself at the home account. Then look at your long mail headers. See what server you are using. If that cures it, then try adding the work server back in. Also, consider checking the "use only this server" checkbox with the appropriate server checked for each account.
Next thing that I would try, if it is still purportedly coming from your work server, would be to launch Terminal.app (in /Applications/Utilities), switch user to an admin-privileged user if necessary (type "su {adminShortUserName}" then type "sudo tcpdump -i en1 port 25". Use en1 if wireless, use en0 if connected by ethernet cable. In this example, I also assume that the smtp port of your personal mail smtp server is port 25. If it is 587 or 465 or something else, use 587 or 465 or something else in place of where I had 25. Now, leave that window open and send a mail from your personal account to you at your personal account. A bunch of stuff should start streaming by in that Terminal window showing the source and destination host names or IP addresses, with either a numeric port number or the acronym smtp. So, let's say you get something where one of the terms is "8.14.193.123.smtp". Switch back into Terminal, type a ^c (control-C) to interrupt the tcpdump, and type one or more of the following (following along my example here): "dig +short -x 8.14.193.123", "dig -x 8.14.193.123", and/or "whois 8.14.193.123". Of course, you will substitute the IP address that you see in place of where I have 8.14.193.123 in my example. That should tell you where your computer is sending your mail.
Post back with the results of the first or both of these things, should you decide to try them out. Then we can try to go forth from there.