Windows Outlook can get nit-picky with uploading/importing large Pst files. Even if someone is able to import a big Pst file, the contents can be really sloppy, with issues like empty inbox, empty emails, loss of headers, etc. You obviously had a big database in Mac Outlook since you used it for 5 years. This means that the Olm file was big, and thus, the converted Pst file was also big. What you can do is try to export parts of your Mac Outlook data to separate Olm files, and convert each Olm file to one Pst file individually. This way you can get smaller Pst files. As can be plainly seen, this might take a bit longer. Other, better, approach is to use "Olm to Pst converter Pro". It's a Mac utility that does what the name implies - converts Olm to Pst file. The way it deals with large Pst file issues is by splitting them into smaller files. This means that you will still have more than one Pst file to import to Windows Outlook, but don't need to archive data to multiple Olm files. This is much simpler and quicker way to not let Pst files get oversized.
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