personal replies marked as spam

Mac OS 10.6.2.

In the past week, I switched from Eudora to Mail.app, so I’m now training SpamSieve with Mail. It’s working fairly well, except that some replies to emails I’ve sent (with Mail) are being marked as spam and I have to happen to see them in my Junk folder. I would’ve expected that these replies would be recognized as Good, since the sender is a recipient of mail that I’ve sent. Is there a way to make sure that previous recipients are automatically whitelisted?

Thanks!

Yes, but first you should check whether the messages are going to the Junk mailbox because of SpamSieve. Since it was working fine before, it seems unlikely that SpamSieve would suddenly start classifying those messages as spam. I wonder if maybe you forgot to turn off Mail’s junk mail filter (there won’t be a Junk mailbox if it’s off).

Sorry, it was my mistake to write “Junk” instead of “Spam.” I do have Mail’s junk filter disabled. Also, I wouldn’t say it was working fine before: I’ve only been using Mail for under a week now, and while SpamSieve is doing a great job of catching spam, this problem with spam-ifying messages from previous recipients has been happening the whole time.

I tried editing the SpamSieve Rule, as in the SS manual 5.2, so that “Sender is not in my Previous Recipients” sends it to Spam. When I did that, suddenly all spam started going to my inbox. As soon as I changed it back to “All messages” go to Spam, order was restored (but presumably I’m back to previous recipients not being whitelisted).

Where am I going wrong? Thanks very much for your help.

Addendum: when I choose “Open Log” or press Cmd-3 in SS, nothing happens, no log opens.

You didn’t mention any problems with SpamSieve and Eudora…or did you only start using SpamSieve when you switched to Mail?

I said that first you should check whether the messages are going to the Junk mailbox because of SpamSieve. What did the log say about those messages?

It would seem that they’re sending spam using the addresses of your previous recipients. I suppose you could clear out the list using Window > Previous Recipients, but this is one of several reasons that it’s generally better to get things solved in SpamSieve rather than whitelisting all the previous recipients.

I’ve never heard of that happening before. You could try using Edit Log. Or open the Console application and navigate it to the SpamSieve log file.

It turns out that my SpamSieve log folder had incorrect permissions, which is why the log wouldn’t open. When I fixed the permissions and opened it, the most recent log was from June. This was obviously a problem, though I don’t know whether it was related to (or the cause of) my original problem. However, I’ll keep an eye on it for a day or so and see if things are working better now.