If, like me, you use Gmail to test and check email authentication results, then you're used to seeing SPF results that say pass or fail. But what does it mean when it says "best guess"?
Here's an example of a Gmail SPF results header that mentions "best guess":
Received-SPF: pass (google.com: best guess record for domain of firstname.lastname@example.org designates 126.96.36.199 as permitted sender)
What this means is that Google's "faking it" -- they are synthesizing a potential SPF record based on what information they can figure out about the domain. The exact rules that go into the synthesized SPF record are unclear. It could be past email history. It could be that reverse DNS between the sending IP address and sending domain match. Or it could be other things. That's not the important bit. The important bit is this: When Gmail tells you "best guess," it means it can't find your SPF record in DNS. That's a problem, and one you should investigate immediately.
In the example above, Gmail is saying that it can't find an SPF record for "b.email.example.com." Google's systems are smart enough to deal with it, so your deliverability to Gmail subscribers is unaffected. But other ISPs do not all have similar "fake an SPF record" functionality. That means that some other ISPs probably will block this same mail due to DNS failures or lack of DNS entries. If you review all your bounces, you'll probably see that this is the case.
And it can be a difficult issue to troubleshoot, if you see those bounces, then test with Gmail, and Gmail says that SPF passes. There's little to indicate that something is wrong, except for that magic phrase "best guess." Keep an eye out for it and know that it's a strong indicator of a potential DNS issue with your sending domain.