Apple Mail Drone Setup for Outlook Mailbox

SpamSieve
, , ,
1

Hello. I’m using SpamSieve and Apple Mail on macOS to filter spam for my Outlook email account. This setup has been working fine for several years. But at some point (I believe coinciding with the major SpamSieve 3 update) my drone setup stopped working. So, I deleted the drone training folders and stopped using that feature. I’m just now getting around to trying to get it working again.

I carefully followed the instructions at 4.3 Drone Setup and Remote Training and see the TrainSpam and TrainGood folders recreated under the Exchange mailbox in Apple Mail for Mac. However, the folders never appeared in the Apple Mail app on my iPhone (iOS) or iPad (iPadOS).

So, I went to 6.3.3.1 Train messages in TrainSpam and TrainGood, specifically the section:

What If I Don’t See the Train Mailboxes on All Devices?

For IMAP accounts, it’s important that the IMAP Path Prefix be set the same way on all devices. Here’s where the setting is located:

  • Apple Mail for Mac: Mail ‣ Settings… ‣ Accounts ‣ [account name] ‣ Server Settings ‣ Advanced IMAP Settings ‣ IMAP Path Prefix
  • Apple Mail for iOS: Settings ‣ Apps ‣ Mail ‣ Mail Accounts ‣ [account name] ‣ Account Settings ‣ Advanced ‣ IMAP Path Prefix

Unfortunately, IMAP Path Prefix does not appear in the indicated path on macOS or iOS. Also, the subsequent tip “If you see the Train mailboxes in Apple Mail on your Mac, but not on other devices, this could be because Mail created the mailboxes but did not sync them to the server. You can fix this by deleting them on your Mac, quitting Mail, and then creating TrainSpam and TrainGood mailboxes using Webmail” only applies to Apple Mail. iCloud Mail doesn’t seem to have any way to add additional mail accounts.

Perhaps I missed something, or maybe drone is no longer possible for this configuration. I understand it’s not supported using the modern Outlook client. But I did use the drone feature successfully a long time ago in SpamSieve version 2.

  • SpamSieve 3.2.2
  • macOS, iOS and iPadOS 26.3.1
2

The IMAP Path Prefix setting is only available for IMAP accounts, not Exchange accounts.

It does not, but presumably you could log into the webmail at outlook.com or wherever your mail provider is. Or create the mailboxes using one of your iOS devices.

4

Sure, I use various email clients and webmail including Outlook for Web on a regular basis. I can manually create the folders in Outlook instead of Apple Mail…

I guess the best approach would be to: (1) shut down SpamSieve, but leave the drone feature enabled (2) in Apple Mail, delete the folders created automatically when I reenabled “Train messages in TrainSpam and TrainGood”, then shut down Apple Mail and (3) recreate the two folders in Outlook for Web. [Sorry, I just had to quickly rewrite this section.]

Hopefully the folders will then successfully propagate from Outlook to Apple Mail. Maybe that’s how I did it years ago but I don’t remember. Let’s see how it goes…

5

Good news: Deleting the TrainSpam and TrainGood folders created automatically by SpamSieve in Apple Mail and manually recreating them in Outlook for Web worked. The folders propagated to all email clients and SpamSieve is correctly utilizing them.

1 Like