Hi @John Scott
Based on the information you shared, I understand that you are making the switch from Mac to Windows after two years and need a way to bulk convert your Outlook data from the Mac format (OLM) to the Windows format (PST).
After looking into the current best practices, the most reliable and free way to transfer your Outlook data from Mac to Windows is actually to use an online email account (like Outlook.com, Exchange, or IMAP) as a "bridge" to sync your data, since Outlook for Mac does not natively export to PST.
Here is the step-by-step workaround you can follow to migrate your data:
First, ensure you are using the Legacy Outlook version on your Mac. Go to File > Export to save your current data.
You will need an online email account with enough storage to hold your data.
- Open Outlook > Preferences > Accounts.
- Click the + icon to add a new account.
- Sign in with your bridge account (Outlook.com, Exchange, IMAP, etc.).
Then, create a New Folder under your newly added online mailbox in Outlook for Mac. Go to File > Import and load the OLM data you exported in Step 1. Once imported, drag and drop all your mail, folders, and calendar items from the "On My Computer" section into the new folder in your online mailbox. Leave Outlook open and wait for the sync to finish.
Note: Before moving to the next step, log into your email via a web browser (webmail) to verify that all your data has successfully synced to the cloud!
Finally, install Outlook on your new Windows computer > Sign in using the exact same email account you used as your bridge > Leave Outlook open and wait for it to sync the entire mailbox down to your Windows machine.
Once the sync is complete on Windows, your data is successfully transferred! If you still strictly need it in a standalone PST file format for backup purposes, you can easily do so from your Windows machine by going to File > Open & Export > Import/Export > Export to a file > Outlook Data File (.pst).
Thank you for your patience.
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