When Apple Mail stops cooperating
peterdannock • 3 Sept 2026 •
I recently found myself wrestling with a problem that many people with large mailboxes eventually face. I use Apple Mail with a Microsoft 365 Exchange account, and over the years my mailbox has grown considerably. What started as a convenient way to manage email became frustrating when messages stopped syncing properly and folders updated slowly. At first, I assumed it was just a temporary issue. However, as the days went on, emails arrived on my phone and in Outlook but didn’t always appear in Apple Mail. Sometimes entire folders would take ages to refresh, and searching for messages became painfully slow. With my mailbox at around 43 GB, I began to wonder whether sheer size was contributing to the problem.
The experience reminded me how dependent I have become on technology working quietly in the background. When it works, I barely notice it. When it doesn’t, even simple tasks can be surprisingly disruptive. I found myself researching sync issues, rebuilding mailboxes, and checking account settings to restore normal service. While I still prefer Apple Mail’s clean interface, the episode highlighted the challenges of managing a large Exchange mailbox. The easiest solution I have found is to use Outlook on Mac instead of Apple Mail. Sometimes the biggest issue isn’t finding the right email application. It’s making sure it can keep up with years of accumulated messages.
Microsoft 365 and Outlook in the same sentence as Apple or Mac makes me cringe. 😆