I haven’t been able to log in securely (which is to say, at all) to download Gmail mail from Outlook 2010 on my desktop since something like February 17. I actually had to switch mail accounts over to GoDaddy in order to get my personal mail. (I use a forwarding service for my primary email address, so I can forward that anywhere I want.) And even at GoDaddy I couldn’t use SSL for logins. It was maddening — all I was getting was an error that said, “Your server does not support the encryption type you have specified”, and the connection would fail.
And yeah, it worked fine in the web browser and on my phone and iPad the whole time.
It was a conundrum. I knew there was nothing wrong with my certificates or anything like that, and what’s worse, Outlook 2010 running on another Windows 7 machine in my office (but hooked up to different accounts) was working fine.
So there matters sat for the last month.
I got to searching around again today for a solution to the problem, and I just completely and accidentally ran across someone saying they had to turn off email scanning in their anti-virus software in order to get rid of this error.
And I thought, fuck me. I upgraded my AV software a little over a month ago. But only on my main machine, not on the other one where things are still working fine (and which isn’t running the same anti-virus suite, for reasons that will soon become evident).
So I opened my copy of F-Secure Client Security 12 (I get a free license for it from the company I work for, that’s why — and only one, so that’s why the other machine doesn’t run it) and looked at the settings. Yes, “Scan and remove viruses from e-mails” was checked. And way over to the side was a URL-ish link that said “Protocols”. Hmm.
I clicked that and was presented with a list of port numbers to scan for POP3, IMAP4, and SMTP. “OK,” said I, “let’s turn off POP3 port scanning,” so I set it to 0, clicked OK, and went back to Outlook.
Worked fine. All that non-existent hair torn out for nothing.
What was truly interesting was that I could SEND email through Gmail just fine. But that’s because I was using TLS instead of SSL, so I wasn’t sending it on port 465, I was (and am) sending it on port 587. And that also explains why I couldn’t make IMAP work on the desktop, either.
I kept beating my head against the wall on this for a month because I really needed to get it working, because I had become used to being able to check my mail on my handheld devices and still download it at home in Outlook (which is where I do most of my email composition anyway; those tiny keyboards don’t work with my fat fingers). The problem with moving things over to GoDaddy is that they only support IMAP on their expensive “Ultimate” Workspace Email product, and I’m using the freebie account that came with my hosting — and they don’t support TLS for outbound SMTP connections, which is really annoying in this day and age.
So in the end, I just turned off the damn email scanning altogether in F-Secure. And I’m embarrassed to say that I should have thought of that in the first damn place, but in partial mitigation, I felt like shite from Christmas till after Valentine’s Day and probably wasn’t thinking all that clearly at the time. It wasn’t till February 24, ironically the day I went to the doctor for my regular checkup, that I actually felt like I’d recovered from whatever I had all that time. And by that time, I’d sure as fuck forgotten all about when I upgraded the AV suite and how that connected with my sudden inability to log in anywhere securely with Outlook.
And besides — who expects a product that’s designed (in part) to keep your email safe to keep your email safe by NOT LETTING YOU LOG IN TO GET IT IN THE FIRST PLACE?