My dad has been using Outlook 2011 with his 2011 MacBook Air running High Sierra. Early in 2021 a change at his e-mail provider caused Outlook 2011 to stop working. He didn't want to spend the money to purchase Office 365 so he switched to using Apple Mail.
Fast forward to a few weeks ago where my sister subscribed to Office 365 and she shared one of her licenses with my dad so that he could begin using Outlook again. The problem is that Office 365 requires one of the last three versions of macOS which are unsupported on his 2011 MBA. I purchased him a used 2015 MBA which can run the current (Monterey) version of macOS. Since the system was shipped to me I installed Catalina (which is the last version of macOS that I have on USB) to ensure he had a clean install. I decided not to perform the update to Monterey as I wanted him to run through the initial configuration with me when I visited him.
We used Migration Assistance to migrate all his data from the 2011 MBA to the 2015 MBA. We ran Apple Mail which updated the Mail information store to a newer version. All is well. I installed Outlook and then attempted to import his Apple Mail mailbox into Outlook. This should be a simple process:
Does anyone know why this would be the case?
I am thinking there's a version incompatibility between the Catalina Apple Mail olm file and that expected by Outlook. I performed some testing at home on my Monterey Mac and I had no issues. When I export the Apple Mail file on my High Sierra system it is in an mbox format which is incompatible with Outlook (i.e. there's no option to use this format). Unfortunately, the MacBook Pro that I would use to perform this testing is no longer working so I do not have a Mac which I can install Catalina on to test this theory (I don't want to downgrade the Mac Pro running Monterey to Catalina only to have to upgrade back to Monterey).
Fast forward to a few weeks ago where my sister subscribed to Office 365 and she shared one of her licenses with my dad so that he could begin using Outlook again. The problem is that Office 365 requires one of the last three versions of macOS which are unsupported on his 2011 MBA. I purchased him a used 2015 MBA which can run the current (Monterey) version of macOS. Since the system was shipped to me I installed Catalina (which is the last version of macOS that I have on USB) to ensure he had a clean install. I decided not to perform the update to Monterey as I wanted him to run through the initial configuration with me when I visited him.
We used Migration Assistance to migrate all his data from the 2011 MBA to the 2015 MBA. We ran Apple Mail which updated the Mail information store to a newer version. All is well. I installed Outlook and then attempted to import his Apple Mail mailbox into Outlook. This should be a simple process:
- Export Apple Mail mailbox to an olm file (the default, the only option)
- Import the export file into Outlook (only supports olm files)
Does anyone know why this would be the case?
I am thinking there's a version incompatibility between the Catalina Apple Mail olm file and that expected by Outlook. I performed some testing at home on my Monterey Mac and I had no issues. When I export the Apple Mail file on my High Sierra system it is in an mbox format which is incompatible with Outlook (i.e. there's no option to use this format). Unfortunately, the MacBook Pro that I would use to perform this testing is no longer working so I do not have a Mac which I can install Catalina on to test this theory (I don't want to downgrade the Mac Pro running Monterey to Catalina only to have to upgrade back to Monterey).
