How set up new IMAP on Outlook-Office 365 and merge in pst from Outlook 2003 for same two email accounts?

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glnz

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Outlook version
Outlook 2019 64-bit
Email Account
POP3
Diane Poremsky's articles on Slipstick are stupendous, but I'm still stumped. What I want to do is complicated.

I want to set up Outlook in Office 365 Home 64-bit on my Win 7 Pro 64-bit machine FOR THE FIRST TIME and have it connect to my two existing email accounts as IMAP. However, I also want to bring in a large .pst file from Outlook 2003 on an XP computer that has many years of emails FROM THE SAME TWO EMAIL ACCOUNTS, to which I have been connecting as POP3 (with "Leave copy of messages on server" always checked). That old .pst file has an email folder setup that I like (including Inbox and Sent but many other folders), which appears on the left side of my Outlook 2003.

Ideally, when I'm done, in my new Outlook in Office 365, I will see the identical email folder setup as before, all my old emails will be there in the same folders (including relatively recent emails in Inbox and Sent), new incoming emails will appear at the top of "Inbox", and new outgoing emails will appear at the top of "Sent". Also ideally, in my new Outlook in Office 365, there will be only one Inbox and one Sent with both old and new emails in each, but all my other folders (with only older emails) will also be there.

In other words, how do I wave a magic wand to transform my good setup in Outlook 2003 on XP into the same setup (without losing any old emails) on Outlook in Office 365 Home 64-bit on my Win 7 Pro 64-bit machine AND from this day forward connect to my two existing emails accounts as IMAP and no longer POP3.

To make matters a bit more complicated, as will probably be familar to you, two weeks ago, when I first turned on Outlook in Office 365 Home on my Win 7 Pro 64-bit machine to take a look, it was very pushy about using its Wizard immediately to connect to Outlook.com or - at a minimum - some other existing email account. I blundered into that (WITHOUT connecting to my two important email accounts), but I have since used Control Panel - Mail to delete the resulting Email Account, Data Files and Profiles (although Profiles now shows "Outlook" as an existing Profile).
I have also gone into C:\Users\[MyName[\AppData\Local\Microsoft\Outlook and renamed the new Autodiscover file as ".old",
and gone into C:\Users\[MyName]\Documents\Outlook Files and renamed the unwanted new .pst files as ".old".
I have NOT yet changed or deleted the .srs or .xml files in C:\Users\[MyName]\AppData\Roaming\Microsoft\Outlook but could certainly do so.
Also, in C:\Users\[MyName]\AppData\Local\Microsoft\Outlook\RoamCache, there are numerous files from two weeks ago that start with "Stream_", but I have not touched them.

SO - HOW SHOULD I PROCEED TO TRY TO DO WHAT I WANT?

(Here is a little more history, but I don't think it's relevant anymore: Until two weeks ago, I had been using exclusively Outlook EXPRESS 6 on my XP machine, and it was great. I also had Office 2003 on that machine, but I had NEVER used its Outlook 2003. To prepare for my intended move to Outlook in Office 365 Home 64-bit on my Win 7 Pro 64-bit machine, I first fired up that Outlook 2003 on the XP machine and -- following Diane's advice here -- I EXPORTED everything from Outlook EXPRESS 6 to Outlook 2003 on the XP machine, still as POP3. That went beautifully, Outlook 2003 is working seamlessly with all my same old folders, and so I succeeded in converting all my old, numerous .dbx files from Outlook EXPRESS 6 into one large .pst file in Outlook 2003. I also moved over my contacts from Outlook EXPRESS 6 to Outlook 2003. All of this so far has stayed POP3. It is that resulting good .pst file that I want to "merge" into a new setup for Outlook in Office 365 Home 64-bit on my Win 7 Pro 64-bit machine with the same two external email accounts as always but now as IMAP not POP3.)

Simple, yes? Thanks.
 
Create the profile in Control panel, Mail. Add the imap accounts to the profile then before opening outlook, switch to the Data files tab and add the pst to the profile. Set it as the default data file.

Adding the pst and setting it as the default data file before opening outlook is important so 'this computer only' folders are not added to the imap data file.
 
Diane - Before I start my Outlook in O365 Home on my Win 7 Pro 64-bit machine, what's the best place to put that .pst file?
Is it C:\Users\[MyName]\Documents\Outlook Files\ ?
I'll have the Data files tab point to it, correct?
Thanks again for very fast answer.
 
Also, since the .pst will be the default data file for the IMAP account in my Outlook, will the very large quantity of old email in that .pst file in its folder setup be synced back up to the email account server? That is, does IMAP cause the email server (a) to copy the folder setup and (b) upload all the old emails?
If the answer is yes, my scheme might not work - there's not enough room in the email accounts in their servers.
 
Diane's advice above is the first clue I've found how to do what I want.

But (after understanding her suggestion) I remain concerned that this might backfire - that (because I will connect to my accounts as IMAP for the first time ever) my old folders and email going back ten years in the pst will be UPLOADED to the email providers' servers, which I don't want.

So, when I add the pst to the initial profile, is there a way to PRE-DESIGNATE its numerous old folders as "(This computer only)"? Would that be a good way to fix my possible issue?
 
I still have the concern above.
Should my existing folders with thousands of emails somehow be in some separate part of new O365 Outlook that will not sync with IMAP? A separate folder list? But right there so I can still very easily open (including attachments), Reply, Forward, copy, etc.?
Thanks.
 
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