User struggles to understand OL 365. Contacts not showing in OL after .pst import to OL 365

Occasional Visitor

In 2017 my laptop was updated to Windows 10 and Office 365. The setting up of Outlook 365 differed from what was familiar and was confusing to me. My impressions were that the setting up of OL 365 was somehow linked both to an email address [in contrast to OL 97, XP, etc where one could set up OL and then set up an email account, if I remember right] and that to even start setting up OL 365, one had to enter an email address to which 365 was associated [or was that to link OL 365 to OneDrive? So confusing]

I copied my data files from that laptop before the laptop’s video chip malfunctioned.

I then uploaded my data files, including the same OL .pst file I used for my old laptop to my new laptop, also running Windows 10 and office 365. When I pointed OL to the same data file to open my Contacts, it showed no Contacts. I confirmed that the file is exactly the same file and size (to confirm it fully saved) as what I used previously.

I can point OL to an older .pst files and the Contacts in that file open fine.

So why do my Contacts from the updated .pst file not open?

We pay for pay for Office 365 support. I have called and spoken w several of your ‘reps’ in the Philippines.  When I’m lucky, I get someone who’s English I can understand. I’ve been told that I need first to export my Contacts and then re-import them in order for Outlook to recognize them. This seems total non-sense, because: 1. It is exactly the same .pst file from which I previous pulled Contacts. The same program should be able to open and run the same data file as before and 2. Outlook opened an older .pst file w no problems.

I’ve had people tell me it’s because I set up Outlook under my gmail acc, which is IMAP and that IMAP requires .ost files, not .pst files.  For reasons I don’t understand, the data file for Outlook on my old laptop was set up under a POP email address.  But for the same 2 reasons described above, I would think this is also an incorrect explanation of why my .pst files wont open. But it does get me really confused and if true, this implies that I don’t understand how OL 365 is fundamentally different from older versions of OL I am familiar with, nor how the email used to set up OL 365 relates to how OL 365 works.  

I recall that the guy who re-set up OL 365 on my old laptop set up Outlook with a 2nd version of my one POP email account which he maybe said was for my data files. It made no sense to me then why I had to have a repeat of my one POP email to hold my Contacts, and he couldn’t explain what and why he did what he did.   I’m vague on this, but it may have to do with this: If I had put my Contacts in IMAP format then it would get saved to the cloud on OneDrive. I work as a licensed Mortgage Advisor and these Contacts have some sensitive, private information on them. So I’m not comfortable posting this info on the cloud where they can be stolen.  Does this have something to do with my present problem getting my Contacts to show up from my .pst file?

I have searched all over the internet for a clear explanation on how OL 365 functions in relationship to the email address used to set it up, but have found nothing useful. I’m no techie, but need to understand how this new OL functions, how .pst, .ost files and the associated email address(es) inter-relate; so a clear, straight-forward explanation would be most helpful for me and, I suspect, many others.

PS:  I just moved the .pst file and imported it into Outlook. I could see it importing different sections of the file. So I do believe the import worked. However, still none of the Calendar items, nor Contacts appear in Outlook.

How can that be?

After earlier pointing OL to my .pst file, which is named for my POP email account, I now have that email address and previously saved emails added to the left side of Outlook beneath my gmail email account name.  How did that get added if I don’t have my Contacts, Calendar items, etc?   [Or maybe those items are there, but I can’t see them ??}   I’m so confused !!

3 Replies



It´s a very tough text to read, if you could explain your problem in Another way with less text.


What exactly is your problem?

It sounds like maybe you just need to right-click on the imported "Contacts" or "Address Book" item in Outlook ==> go to "Properties" ==> click the "Outlook Address Book" tab ==> then check the "Show this folder as an email Address Book" box.

@Tony Derricott 


You can try an automated utility that can help you to read all entire .pst email content like contacts, notes, calendar, outbox and other email items, and provide option to migrate to Office 365 in a professional way with HFS (hierarchical folder system) of .PST database with authenticity. You can give it a try