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@Macbookprodude A while ago I tried to get os9 connected as much as possible.
AFAIK the only useful/working email-client I found, was the one included in Classilla [ #30 ].
Here's more about file sharing between os9 and newer Mac [ #1 ] and about useful software [ #17 , #9 and the G3 Worstation Wiki].

So outlook express won’t work ? I can try Classila - what are the ports for IMAP gmail ?
 
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So outlook express won’t work ? I can try Classila - what are the ports for IMAP gmail ?
You have to follow Gmail's IMAP-setting recommendations. Same for iCloud, Outlook etc.
And you have to create a unique password for 2FA like @iluvmacs99 mentioned above. Same for gmail, icloud, outlook etc too.
 
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