Gmail – How to quote several parts of email in Gmail

The problem seems to be what IMAP client is used to copy the messages into gmail. This is a known issue where the IMAP client does not specify the internal date of the email and the server defaults to the current time.

In my case I was attemping to copy old courier Maildir folders into gmail. I ended up using this link that gave direction on how to have Mutt do the dirty work of converting Maildir to mbox. I then used this script from github to accomplish copying the mbox files into gmail. The results were perfect although I did have to boot up an Ubuntu virtual machine to accomplish this.

Alternatively, use a different IMAP client to see if it appends the correct date.

Answering my own question, it turned out the problem was during switching from rich formatting to plain text:

• if previously I used plain text, Gmail will break long lines properly
• if previously I used rich formatting, Gmail will quote Outlook style, and when I press 'plain text', Gmail will reformat the reply to plain text, but long lines are not broken

So the solution if previously I chose rich formatting is:

• reply
• click 'plain text'
• discard
• reply again