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Importing Data into Outlook.com

I'm currently tasked with importing a huge number of Emails from proprietary mail system into an Outlook.com account (yes, the web service not the desktop app).

Due to the proprietary nature of the source system and the fact that all emails require custom pre-processing prior to importing them into Outlook.com, any commercial service is not an option. Importing the data into a local Outlook database and then export it to Outlook.com is probably not an option either since this is meant to run server side.

What would be my best option to implement the actual import step that preserves the actual email timestamps as they were when the mail was originally received?

This is not for a large number of accounts but this is how you do it for a single account. I would recommend reaching out to Microsoft for support especially if you are a paying customer that needs to import this data.

According to Outlook.com IMAP is not supported yet. Outlook.com does support ActiveSync . I'm not sure which proprietary mail system you are using but it appears that only method would be to setup ActiveSync on the desktop (Outlook) then add a second account (proprietary mail system) via IMAP, then to drag-drop the contents between the two accounts. This is a common method to migrate email data.

Secondly, you can login into your Outlook account and set it to import 3rd party email. Here is an article showing how to do that, Move Your Mail to Outlook article.

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