Hi Ryan Pistorius,
Welcome to Microsoft Q&A Forum!
Have a good day and I hope you're doing well!
I totally get your frustration. It's really aggravating when updates break something you've relied on for years, like opening .msg files for client evidence. I'm sorry this has been such a headache, and thanks for detailing it; it helps spotlight these issues for the community.
As you pointed out, Microsoft has shifted focus to .eml as their preferred format (which, as you noted, doesn't always play nice with Mac Mail), but they've removed even basic read-only support for the older .msg format in the "New" Outlook for Mac. This stems from Outlook for Mac's different architecture compared to Windows. It's a known limitation where macOS doesn't natively handle .msg files the same way, leading to that useless "new email with attachment" loop you described.
From research and similar user reports, here are some workarounds that might help. You mentioned trying to open and send the files to yourself, so these build on that starting with the most reliable option:
1. Revert to Classic Legacy Outlook for Mac: This often resolves the issue by allowing direct, full access to .msg files. In New Outlook, go to the menu bar > Outlook > Revert to Legacy Outlook. Once switched, drag the .msg file into the app or right-click and select Open With > Outlook.
2. Use the Outlook Web App: Email the .msg file to your Outlook.com account, then open the attachment via the web to view it. To set Outlook as default: Right-click the file > Open With > Other > Check "Always Open With" > Select Outlook > Open. Note that this is only partially helpful and requires a Microsoft account (like Outlook.com).
3. Open with TextEdit: For a quick text peek (though it may show gibberish), find the file in Finder > Right-click > Open With > TextEdit, and scroll for readable content.
4. Change the File Extension: Since you mentioned .eml, this could be a good next step. It's not exactly what you described trying, but it leverages that format. Rename the file from .msg to .eml (Right-click in Finder > Get Info > Expand Name & Extension > Change to .eml). Then, open it in Apple Mail or Outlook; it often works well for simpler files without the attachment loop.
If these don't cut it, I know there are third-party tools that can assist with viewing or converting .msg files, but as a moderator, I can't point you to specific ones. You can easily find them by searching online for "MSG viewer for Mac."
I truly appreciate your feedback, insights like yours are invaluable and directly help us improve products like Outlook. To get this in front of the Microsoft product team quickly, I encourage you to submit feedback directly. This can amplify your voice and influence future updates: Within the Outlook app: Go to Help > Feedback > Report a problem (be sure to include your Outlook version, macOS details, and steps to reproduce the issue, such as trying to open a .msg file and observing it creates a new email with the file attached instead of displaying the content) or through the Microsoft Outlook Feedback Portal.
Please know that while our initial response might not resolve the issue right away, your input is incredibly valuable. I hope this information helps resolve your issue to some extent, and I truly empathize and understand it. If you have any questions, or if I was unclear or misunderstood something, feel free to let me know. I'm here to help!
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