Solved Outlook 2021 - Switching from POP3 to IMAP Issues.

I've always ever had my MS Outlook e-mail setup via POP3 on my Windows 8 (then Windows 10) laptop. I've never had any issues backing up and restoring my POP3 emails from install to install, or even machine to machine.

The change now is that I now have my old-ish laptop (Windows 10) with my POP3 e-mail account setup, as well as a recently purchased desktop PC (Windows 11).

Where e-mails are concerned, the intention is to have an exact duplicate of the single e-mail account, on both machines, which should include Inbox, Sent, Contacts & Calendars.

I've backed up the POP3 to a backup.pst file, and also copied the actual PST data file that Outlook was using to sync to.

I then deleted the old POP3 account so I could start afresh with the IMAP settings on the laptop first since the desktop is still having some last bits of software installed on it.

When I import the backup.pst file into the IMAP settings, I let Outlook do what it needs to, and then I noticed a few annoyances that I need fixed:

1) The backup.pst's sent folder was stored in the Sent Item (This Computer Only) sub-folder, unlike how it works for the Inbox.
The issue with this, if this happens on my desktop also, is that my sent items will not be the same, depending on which computer I use to send e-mails from.

2) Contacts are stored in a Contacts folder, which matches what I had in my backup.pst. However, there's also a Contacts (This Computer Only) which I'm not sure what the purpose/use of is exactly, and my concern is which one will be used as default when either creating a new contact or creating a new e-mail. I already tested creating a new e-mail, and Outlook does not see the Contacts (will all my contacts in it) location, and only sees the Contacts folder which is empty.

3) Calendar is a similar issue, where I have two calendars, one on the computer and one which I believe syncs via the IMAP settings. The Calendar (This Computer Only) is totally empty and all my previous and future calendar entries are populated inside the Calendar folder. The challenge with this is again, which will Outlook default to, and how do I keep my calendars synced?

I would think it might be as simple as moving the sent items to the empty Sent folder and leaving the "this computer only" sent items as is since I will be importing the backup.pst on both machines anyway. I'm just needing to know what will happen in day-to-day usage.

The same concerns apply to both the contacts and the calendar, and how to manage the two locations for these.

Any tips on the above would be appreciated.

Hi and welcome.

It is a bit of a pain to switch and seems a bit awkward at first.
You are right about the duplication of some folders named 'this xxxx'.
Give it a bit of time, you will find out that IMAP is much more flexible and convenient than the old static POP.
You will see in time that some folders can be deleted.
The old mail box will no longer have to be carried with you as you switch systems.
But now that you have switched and that all the content has been or will be carried over to IMAP,
you will never have to do this again.

I hope the article below answers some of those questions.

OAT said:

Hi and welcome.

It is a bit of a pain to switch and seems a bit awkward at first.
You are right about the duplication of some folders named 'this xxxx'.
Give it a bit of time, you will find out that IMAP is much more flexible and convenient than the old static POP.
You will see in time that some folders can be deleted.
The old mail box will no longer have to be carried with you as you switch systems.
But now that you have switched and that all the content has been or will be carried over to IMAP,
you will never have to do this again.

I hope the article below answers some of those questions.

Email - POP to IMAP transition in Outlook - Saffire Knowledge Base

At this point, you should have already determined that your email is set up as a POP account in Outlook. If not, please go to this page to determine which prot

support.saffire.com

Click to expand...

@OAT - Thanks for the welcome.

Yeah, I'd been hesitant for ages now in doing the switch from POP3 to IMAP, but I never had the need (i.e. multiple devices) so I never bothered with it. I've heard similar sentiments to what you shared about how convenient IMAP can be. So let's see what this brings.

Thanks for the link, it answered the issue relating to the sent folder, since I can essentially just drag and drop them from the "This Computer Only" folder onto the folder that will sync across devices.

I'm not too sure if the same applies to moving the contacts and calendar from the synced IMAP folders to the "This Computer Only". I know this sounds silly, but the only reason I'm thinking of doing this is that Outlook 2021 doesn't see (or show me by default) the IMAP information for the contacts and calendar. Unless there is a way of forcing Outlook to default to the IMAP synced contacts + calendar, as opposed to the now empty information within Outlook?

Update:

I've managed to make some progress through either trial and error, making contact with my mail hosting provider, as well as doing some additional reading by myself.

I have resolved the setting up of e-mails (incoming and outgoing) and all is syncing as it should (apart from one annoying glitch which I'll leave for another post).

As for syncing contacts and calendars, I've read and was also informed by my mail hosting provider that these are not supported, so I'm okay with managing these manually on each computer (there are only 2 computers anyway).

And the above is based on not wanting to buy an application that would allow me to sync these two items, as I don't think it's such a headache if it does leave me a manual option at this stage.

Unless there are free apps that would sync contacts and calendars, I haven't done much searching on this as yet.

So I'd say my issues are resolved, to a point.

OverDose said:

As for syncing contacts and calendars

Click to expand...

For that you would have to set the email account in Outlook up as EAS/Exchange rather than IMAP.

Denis

Try3 said:

For that you would have to set the email account in Outlook up as Exchange rather than IMAP.

Denis

Click to expand...

@Try3 - Yeah, I read as much, but as my mail hosting provider confirmed, they only offer POP3 and IMAP as mail hosting options.

So I'll have to live with the manual management of this and hope that it doesn't become a headache.

I have stuck with POP mail retrieval.

If I understand IMAP correctly, your Calendar and possibly also Contacts are still stored in a pst file [whilst your email headers are in an ost file].
So I assume you now just copy your pst files across to your other computer whilst Outlook is closed.

Denis

Try3 said:

I have stuck with POP mail retrieval.

If I understand IMAP correctly, your Calendar and possibly also Contacts are still stored in a pst file [whilst your email headers are in an ost file].
So I assume you now just copy your pst files across to your other computer whilst Outlook is closed.

Denis

Click to expand...

Correct, for the initial setting up, which is what I've done.

I was thinking about managing new entries post-initial setup and making sure that irrespective of which machine I would be using to send/receive e-mails from, the manually managed information would have to match, so I don't miss any calendar meetings (I have a plan for this already) or not have contacts that one machine has and the other doesn't.

I RoboCopy my PST files between my computers.
- Outlook must be closed on both computers for this to be done. Whilst including a test for it being closed on the current computer is straightforward, I could not find an easy way to test on one computer that it was closed on another computer [everything I tried turned out to be unreliable]. So I just have to check myself instead.
ROBOCOPY "F:\Where ever\*.pst" "\\OtherComputer\Shared folder\OL subfolder" /MIR /DCOPY:DAT /R:10 /MT:32

The :MT setting can really speed up copying. I chose 32 as my 'default' value after trying different values until I found the best one for my computers.
:MT sets the number of threads in use in parallel and so cuts out much of the idle time you'd get if copying using xcopy or similar.

All the best,
Denis

Try3 said:

I RoboCopy my PST files between my computers.
- Outlook must be closed on both computers for this to be done. Whilst including a test for it being closed on the current computer is straightforward, I could not find an easy way to test on one computer that it was closed on another computer [everything I tried turned out to be unreliable]. So I just have to check myself instead.
ROBOCOPY "F:\Where ever\*.pst" "\\OtherComputer\Shared folder\OL subfolder" /MIR /DCOPY:DAT /R:10 /MT:32

The :MT setting can really speed up copying. I chose 32 as my 'default' value after trying different values until I found the best one for my computers.
:MT sets the number of threads in use in parallel and so cuts out much of the idle time you'd get if copying using xcopy or similar.

All the best,
Denis

Click to expand...

Thanks for this. I'll have a look as to whether this is viable for what I'd be doing. Because I can as easily just export Contacts + Calendar from one machine, and then import only those entries onto the other machine, which would be a very basic form of "manual syncing".

And because it's not a large amount of contacts and calendar entries, it wouldn't take more than a few minutes.

OK.
I just run a script that runs the RoboCopy for me. I don't have to do anything within Outlook itself, I just close it.


Best of luck,
Denis