C-Command Software Forum

SpamSieve Thrashing Outgoing Mail

I’ve been puzzled and frustrated by a problem I’ve been experiencing with SpamSieve. First off, I have followed the set-up instructions for Entourage 2008 to a tee, and I’m using Google’s Gmail service with IMAP configuration. I am only using the two rules that are recommended in the SpamSieve manual for IMAP configuration using Entourage 2008. Why is SpamSieve filtering outgoing mail and putting it in the Junk folder? I have sent out about 10 emails, some more important than others and, instead of appearing in the Sent Mail folder as they should, SpamSieve is filtering them and placing them in Junk. Several of these messages are replies to mail already received, but it’s also occuring with new sent mail. I’ve had to go back and perform a search using Entourage to discover the mail on my local drive (root mail folders) and attempt to move it back, which usually doesn’t work I presume because Entourage doesnt want to allow additional rules to be applied after SpamSieve processes mail, or perhaps because SpamSieve is re-processing that mail based on its database and its rules are trumping my commands in the contextual menu to treat as “good” and “move to Sent Mail”. If I attempt to return to Google’s servers to resurrect my mail, I often find it in the Spam folder and return it to the Inbox but have had little success returning it to its proper place in the Sent Mail folder.

Last night, I sent out two replies to items posted for sale on Craigslist. Guess what? SpamSieve dispatched them to Junk within seconds after I sent them. Last week, I sent a completed bank form to my brother. Once again, SpamSieve transferred this sent message to Junk mail. Two weeks ago, I sent some important documents to the Admissions office of a University only to discover that the sent mail went out but landed in Junk Mail instead Sent Items. And this behavior seems so arbitrary and unnecessary. I really don’t want, nor do I see a point, in my outgoing (sent mail) being filtered. If anything, I can see the utility of having SpamSieve filter outgoing for the sole purpose of lifting the metadata so that mail from that recipient is added to the list of good mail, but if this comes at the expense of having SpamSieve spoil good outgoing mail, it isnt worth it. Until there’s a more permanent solution, I have opened the corpus and deleted all words, associations or connections to Craigslist. I also went in and deleted my brother’s email address and all words associated with it. I did notice that the corpus had these items as both good and bad. Is there a rule that will obviate the need for this type of tinkering? For example, might I place a rule before all others in Entourage that will prevent SpamSieve from filtering Outgoing mail. If you can indulge in a better solution, I would be grateful.

One Other Matter:
Why does SpamSieve block mail from a merchant with whom a purchase was just made? I just purchased a hard drive from an online merchant and the receipt and shipping information were emailed and showed in the Inbox for a short time. SpamSieve transferred this legitmate message to Junk Mail. Must I go in and add online merchants to the whitelist to prevent these types of errors?

Thank you.

Regards,
RG

Perhaps you could post some screenshots of your Entourage setup. Otherwise, I claim that it works if you follow the instructions, you claim that you followed the instructions, and we don’t get anywhere.

I’ve never heard of that happening before. It’s only supposed to filter incoming messages. I can only guess that you created the rules in the “Outgoing” tab of the Entourage’s Rules window instead of (or in addition to) in the “Mail (IMAP)” tab.

I don’t understand what’s going on here.

  1. Why do you have to search, if the messages are in the Junk E-mail folder?
  2. You should first train the messages as good, and then move them. (For POP messages, Train Good will move the messages to the inbox.)
  3. What do you mean when you say that moving doesn’t work? What happens when you try to drag and drop the messages?
  4. No rules of any kind are involved after the messages have been received or sent. Neither is SpamSieve (since it’s only activated by rules).

I’m not sure why that would be, since the Spam folder is for Google’s spam filter; it’s not used by SpamSieve or Entourage if you followed the SpamSieve instructions.

Ordinarily, SpamSieve should classify these messages correctly without your having to modify the whitelist. However, if lots of previous messages were mistakenly classified as spam (and perhaps were not all corrected using Train Good) then SpamSIeve will be working from incorrect information, so it’s not a surprise that it would make more mistakes.

I think the first step should be to make sure that the setup is correct, so that it’s processing only the incoming messages and that they’re going into the expected folders. After that, you could reset SpamSieve’s corpus and then re-train it so that we can be sure it’s working from correct information.

Your commitment to support is appreciated and unprecedented. It is Easter Sunday, after all. Thank you, Michael.

Perhaps you could post some screenshots of your Entourage setup. Otherwise, I claim that it works if you follow the instructions, you claim that you followed the instructions, and we don’t get anywhere.

I’ve posted set-up screenshots of SpamSieve and of most aspects of Entourage set-up and IMAP configuration. I also included a snapshot of my sent mail (Craigslist) showing the message for the ElGato product and some furniture both as sent mail and in my inbox. I don’t understand why my brother’s email or craiglist would even appear in the corpus as bad. I’ve never marked either one as bad, nor would I ever receive mail from those sources that I would want filtered. After informing SpamSieve 3-4 times that these messages were good and then moving them by both drag-and-drop and contextual, they still did not show up in the Sent Mail folder where they resided originally. I went to Google’s server and discovered the messages in the folder “Deleted Items”. From the “More Actions” drop-down menu, I chose to apply the label “sent items” since there’s not an option to move mail to Sent Folder. Gmail applied the label and moved the messages to my Inbox where I yet again moved them to Sent Mail within Entourage. I don’t recall if I used contextual or drag or drop this last time.

I’ve never heard of that happening before. It’s only supposed to filter incoming messages. I can only guess that you created the rules in the “Outgoing” tab of the Entourage’s Rules window instead of (or in addition to) in the “Mail (IMAP)” tab.

I wish there was an easy explanation. Despite my experience with computers/software and following simple instructions (and being intelligent), there is the possibility I made a mistake, although I have not noticed one yet.

I don’t understand what’s going on here.

  1. Why do you have to search, if the messages are in the Junk E-mail folder?
  2. You should first train the messages as good, and then move them. (For POP messages, Train Good will move the messages to the inbox.)
  3. What do you mean when you say that moving doesn’t work? What happens when you try to drag and drop the messages?
  4. No rules of any kind are involved after the messages have been received or sent. Neither is SpamSieve (since it’s only activated by rules).

The reason I must search is b/c of the shear volume of the junk mail folder makes it impractical to go through every message, and these messages have also been located in the Inbox folder of the local folders “On My Computer”. I’ve tried moving and dragging and dropping. Both options result in SpamSieve moving the message to my root folder “On My Computer” Inbox. Before I attempt to move them, I train SpamSieve. Something odd is occurring b/c once GMAIL and my folders attempt to sync I’m getting clones of the moved messages in the Inbox/Junk Mail folders “On My Computer”.

I’m not sure why that would be, since the Spam folder is for Google’s spam filter; it’s not used by SpamSieve or Entourage if you followed the SpamSieve instructions.

I’m not sure either, Michael. It’s been frustrating. I cannot fathom why SpamSieve is filtering outgoing mail. I do have confidence in you and in your products, in any case.

Regards

This all looks fine.

Probably what happened is that SpamSieve processed an outgoing message, thought it was borderline spam, and so it auto-trained it as spam. You didn’t immediately notice this, since you weren’t expecting outgoing messages to be filtered, so the incorrect training remained in the corpus. Since it won’t be processing outgoing messages going forward, I wouldn’t worry about this. Just reset the corpus and get a fresh start.

This is because you have Entourage set to move the spam messages to the Junk E-mail folder On My Computer. Since this is a local folder, moving the messages entails deleting them from the IMAP server. Thus, the server versions of the messages appear in Deleted Items.

I think I’ve figured it out. This odd behavior hinges on two unusual aspects of your setup:

  1. Entourage, unlike most other mail programs, seems to apply its rules to all new IMAP messages, not just ones that arrive in the inbox. Of course, it’s smart enough not to apply the (incoming) rules to new messages in the Sent folder.
  2. Gmail has an odd notion of IMAP folders. What seem like individual messages to you can appear in multiple IMAP folders at once, and from an IMAP perspective these copies are distinct messages. In particular, all messages (even sent messages) appear in the All Mail folder.

Putting these two together, if you’re using Entourage and Gmail’s IMAP, copies of your sent messages will appear as new messages in the All Mail folder, and Entourage will apply the rules to them.

To prevent SpamSieve from processing the sent messages, you could change the criterion in your “SpamSieve - Move If Spam” rule from “All messages” to “Folder is Inbox (Gmail).”

This is because you have Entourage set to move the spam messages to the Junk E-mail folder On My Computer. Since this is a local folder, moving the messages entails deleting them from the IMAP server. Thus, the server versions of the messages appear in Deleted Items.

I surmise that using “On My Computer” Junk Email folder may also explain why my Entourage 2008 database (1.9GB) is almost double the size of the 2004 database or is this soley the result of choosing IMAP over POP, since IMAP stores messages locally? Doesnt seem like Entourage dynamically sizes the database. Maybe I could change the server settings to immediately delete junk mail. Do you think I should change the SpamSieve move location to Gmail’s “Spam” folder instead?

  1. Gmail has an odd notion of IMAP folders. What seem like individual messages to you can appear in multiple IMAP folders at once, and from an IMAP perspective these copies are distinct messages. In particular, all messages (even sent messages) appear in the All Mail folder.

Indeed, Gmail’s IMAP implementation is unusual.

Thanks again, Michael, for sorting this out.

POP also stores the messages locally. I suspect the doubling is because Gmail stores each message in at least two folders (the normal folder plus All Mail). Entourage sees these as distinct messages, so it stores them twice.

I think it’s most efficient to get them off the server into the folder On My Computer.