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Will I be able to convert from windows desktop 2014 to Mac 2019?
Welcome, @Nash2be and thank you for coming to the QuickBooks Community for assistance. I have some insight on converting from the windows to mac version to pass along.
The best way to convert to Mac from Desktop would be to use the newest versions of each, you can find the steps here.
You may need to upgrade to a newer version of QuickBooks Desktop for the convert to be successful. Here is a link to the trial version for you to download.
If you have any questions about this process, please feel free to reply to me here. You also can call support, here, if you'd prefer someone walk you through the process step by step.