> So what’s happened here? Well, whoever collected these emails first converted from CRLF (i.e., “Windows” line ending coding) to “NL” (i.e., “Unix” line ending coding). This is pretty normal if you want to deal with email. But you then have one byte fewer:

I think there is a second possible conclusion, which is that the transformation happened historically. Everyone assumes these emails are an exact dump from Gmail, but isn't it possible that Epstein was syncing emails from Gmail to a third party mail server?

Since the Stackoverflow post details the exact situation in 2011, I think we should be open to the idea that we're seeing data collected from a secondary mail server, not Gmail directly.

Do we have anything to discount this?

(If I'm not mistaken, I think you can also see the "=" issue simply by applying the Quoted-Printable encoding twice, not just by mishandling the line-endings, which also makes me think two mail servers. It also explains why the "=" symbol is retained.)

Yeah, I wouldn't bet on this being a single bad Gmail export; it smells much more like the accumulated scars of multiple mail systems doing "helpful" things to the same messages over time

In one of the email PDFs I saw an XML plist with some metadata that looked like it was from Apple's Mail.app, so these might be extracted from whatever internal format that uses.

This seems like the most likely reason to me!