Depending on your service provider, to import SENT messages using Gmail's POP import tool the source messages need to be in the INBOX at the old provider.
This is because Gmail's POP access is to the INBOX only. This assumes that the source account stores the messages in a traditional format (MBOX, etc.) rather than labeling like Gmail.
On Gmail's end the distinction between a message in Sent, and one that is not, is quite simply the FROM Address. In other words, if Gmail recognizes a FROM address as belonging to you (including aliases and "Send As" accounts), it will show up in SENT. It doesn't matter if it actually was sent by Gmail. You can't add or remove messages from SENT.
When migrating large numbers of messages from one account to another I would typically batch them by source folder and then, on Gmail's end, apply different labels for each batch using the POP import tool.
Example:
- Copy the messages from a source folder into the source account's INBOX
- Import the messages to Gmail using POP, removing the original (it was a copy) and applying a label matching the original folder. The original message is removed so that I know all the messages successfully transferred.
- Copy another folder to the source INBOX and repeat the import with a different label.
Most of my migrations have benifited from having FTP access to the source account (cPanel) to move messages around, and this aporoach has been reliable.
I believe POP import to Gmail will do about 200 per sync so larger folders need multiple syncs to transfer.
The devil's in the details and there are many tools available. But, if you can move messages around without modifying them, it is IMO preferable.
Notes
- The POP import tool preserves the original message and headers which is why I like it.
- It may or may not be obvious, but the messages' read status would not be carried over.
- You can address this globally by searching using the label(s) you apply during import and then batch update the status of all the messages to "read".
- Presumably for a mailbox migration this would be of little concern, however, if you want to maintain the actual read status (rather than globally setting all to read), you can batch import read and unread messages separately so that a custom label can be applied and the correct read status reapplied following import.
- When importing via POP, Gmail will apply SPAM filters.
- You may be able to create a rule to override this,
- or, by searching the SPAM using the label(s) you apply during imports, and removing the SPAM label,
- or, if your SPAM box is emptied prior to importing you may simply be able to visually see the new messages in the SPAM folder and remove the label.