Mail rules run amok!
A friend of mine, Larry, asked for a little help with some various email and sync problems. On a Zoom call with him, I diagnosed it, helped him find the correct settings, and then we promptly deleted his email account and all his thousands of stored messages. (There’s a twist at the end.)
Let’s rewind.
Larry encountered something I’ve seen many times over the last couple of decades, including inflicting it on myself. Email hosts, DNS hosts, webmail interfaces, and email apps can all make it easy to write a rule to file or forward email in a way that you only notice when something appears off. This is typically when emails you expect stop arriving or appear in the wrong place.
Tracking down the problem can be difficult because of the multiple locations in which you may have written a rule or enabled a forwarding feature, which may include all messages, or have provisions that filter certain messages.
In Larry’s case, he has a standalone multifunction printer that can email him scans. However, all his scans show up in the trash folder of a different email account than the one to which he is sending the files! Larry wrote:
Some emails have an unpredictable habit of disappearing from my inbox. I’ve turned off all the spam filtering I can think of, but still things wind up in trash without my intervention. I’ve taken to flagging emails I don’t want to lose so I can at least go retrieve them from the Flagged folder.
I suspected this was being caused a rule of some sort. My normal cascading process for figuring this out is:
- Check the email app’s rules. Email apps that let you set rules or filters almost always have a single location where you can review all these mail manipulation instructions. In Apple Mail: Mail > Settings > Rules. For instance, I have a rule to file old email into an archived mailbox.
- Look over spam-filtering options. Overaggressive spam filtering can automatically drop messages into the trash. The new MailMaven app lets you use MailMaven > Settings > Process > Junk to perform specific actions depending on the SpamSieve mail-analysis app’s score. That include moving messages to the Trash.
- Examine host rules. Mail hosts often let you create rules that apply to messages arriving at the server, regardless of which email client you use to receive them via POP or IMAP. You can see this phenomenon in action: a message arrives in your email app, then suddenly disappears. That’s the server running its rules for your account, and moving the message from one mailbox to another, or forwarding it and deleting it. More on this below.
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Tame server-based junk filters. Gmail and others have become quite aggressive in fighting spam by filtering messages that are clearly “ham.” Have you seen the phenomenon lately where messages to someone with whom you regularly exchange emails wind up in their filtered mailbox? If you see that on your end, check the host’s filtering setting just as you would in an app, and adjust to get the right balance.
Larry’s problem was certainly one of the above, and because his incoming messages to one account were being deleted and then showing up in the trash of another account, we first checked his email app. No rules were in place, which meant server-side forwarding was the culprit.
I’ve found that this bites Apple email users quite often, because Apple lets you set rules at iCloud.com that cannot be viewed elsewhere. You have to log into iCloud.com, choose Mail, then click the gear icon at the top of the Mailboxes sidebar. Finally, choose Rules. Check that a rule here isn’t sweeping in more than you expected.
Larry wasn’t using iCloud for this purpose, so we visited his mail host via a control panel he rarely needs to use as he only employs a fraction of the features offered by the host. We found his email account, found that all messages sent to larry@a.com were being forward to larry@b.com. He clicked a gear icon, clicked Delete, and confirmed—only then realizing that the poorly designed interface had directed him—and allowed him—to delete his entire email account, not the forwarding rule.
Fortunately, he had Time Machine backups, and his internet host automatically performs full account data backups each night. His email was restored with a click. Whew!
However, you might see a logical problem in the above. If his email was all being forwarded to another account, why didn’t Larry notice before his scans started appearing in the Trash mailbox of that second account?
Apple Mail, like most modern email apps, offers a unified mailbox called All Inboxes that combines the contents of each inbox in configured accounts. It looks and acts like a single mailbox. Larry uses that for his email, as do many people. He never noticed, nor did he need to, that emails to larry@a.com showed up in the inbox of larry@b.com, because in All Inboxes, all incoming email is equal. It’s only when b.com (not its real name) began to filter aggressively that we unknotted the thread that was tying one account to another.
Fortunately, Larry is one of the calmest people I know, even when I helped him delete all his email. His reaction: “You solved the problem.” We all need friends like that.
[Got a question for the column? You can email glenn@sixcolors.com or use /glenn in our subscriber-only Discord community.]
[Glenn Fleishman is a printing and comics historian, Jeopardy champion, and serial Kickstarterer. His latest books are Six Centuries of Type & Printing (Aperiodical LLC) and How Comics Are Made (Andrews McMeel Publishing).]
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