I taught a class recently with Fritz and Aaron and . By the end of our time together, Aaron had convinced me that Google was the greatest thing since sliced bread (or at least that it greatly simplified his life). Of particular interest to me was the use of Gmail as a sort of email proxy; sending & receiving all email via my Gmail account. Although there are a lot of other benefits, of particular interest to me was the spam-scrubbing effect of this configuration.
Since I was dumb enough years ago to post my email address for all the world to see right on my homepage, and include links to that page in all my newsgroup postings, and supply my email address to countless financial & other organizations without really thinking about the consequences, my spam volume grew over time to about 300 messages per day. I'd been using POPFile for the past couple of years to combat that, but since it's local proxy (not a server-side antispam filter) I still had to go through the motions of downloading the email in order to throw it away. So I'd reached the point that Aaron did where I was thinking about killing my original bearcanyon.com email address and starting over fresh.
So I was primed for conversion when Aaron started giving me the live tour of his newfound Google nirvana. So when I got home, I pointed Outlook at Gmail (and also installed Google Desktop and Google Earth which, by the way, is tres cool for looking up driving directions). But I digress.
I've since encountered two very annoying issues with Gmail's SMTP/POP service:
- My posts to list servers don't show up in my own inbox.
- Gmail's SMTP & POP servers overzealously reject messages they deem 'unsafe'.
Quirk #1 means that whenever I post to an email-based discussion list, my post to the list never shows up in my inbox. This means that the only way I can tell if my post went through to the list is if/when someone replies. But if/when they reply, I'll only see the contents of their reply; not my original post. For whatever reason, this drives me absolutely crazy; because I can't tell the difference between a post that's been moderated out, or otherwise didn't make it to the list, and a post that went through just fine. I originally thought this must be a small bug in their smtp/pop support, but was disappointed to learn that this behavior is actually by design. Apparently I'm not the only one who thinks this is a silly feature, or at best a feature that users should be allow to enable/disable. That guy has resorted to using 2 gmail accounts for list subscriptions: one that he uses exclusively to post to lists with; the other that he uses exclusively to retrieve/read posts to that list with.
Quirk #2 also really burns me. But unlike quirk #1, which is still mostly just really annoying, this quirk actually costs me time. As a developer that consults and delivers training, I email people code on a fairly regular basis (samples, proofs of concept, code I've reviewed, fixed up, and sent back, etc..). But the day after switching to Gmail for all my email sending & receiving needs, I sent a bit of code (with prebuilt binaries included) to one of the students who had attended the class I'd just finished teaching. But a few winks after sending the email, a message showed up in my inbox that looks like this:
Your message did not reach some or all of the intended recipients.
Subject: <subject>
Sent: <date time>
The following recipient(s) could not be reached:
'John Doe' on <date time>
552 5.7.0 Illegal Attachment <GUID-like thingy>
The email was from “System Administrator”, and attempting to view the email headers in Outlook resulted in nothing. There appeared to be no headers whatsoever that would explain what server it was that bounced my email, or who this mysterious system administrator might be. If it hadn't included the correct subject of the email I just sent, and the correct recipient name, I would have figured it was some sort of malware that had gotten itself embedded into Outlook somehow.
It turns out that it was Gmail's SMTP server that refused to send my email. I've had other people's email servers reject emails from me as they arrived because I'd done something like attach an EXE directly to an email message. But this was the first time that I'd had my own SMTP relay refuse to send an email of mine due to an attachment. Even odder to me was the fact that the only attachment I'd included was a single ZIP file. Why on earth would my own SMTP relay refuse to send an email on my behalf just because I had attached a zip file?
Again, it turns out that this behavior is by design. The issue with my email was that the ZIP file I'd attached had a DLL in it (3 directory levels deep: project\bin\debug). So Gmail's SMTP relay is recursing its way through ZIP attachments, looking for files with .DLL, .EXE, and who knows what other kind of extensions. If if finds just one, it refuses to send it. This really chaps my hide. If somebody gets an email from someone that has a ZIP file attached, and they want to double click it to open it, then drill into it to find an EXE in there and double click that to run it, more power to them. Why should Gmail take it upon themselves to refuse to send a ZIP file to someone just because it has an EXE or DLL somewhere inside of it? Or refuse to deliver email to me from someone else for the same reason? I think they're solving a problem that doesn't exist. And it costs me time.
So now I'm forced to either delete intermediate build output if I just want to quickly send someone a code fragment. But then they have to have the right build tools in order to recreate the library/exe I was trying to give them. Sometimes that's not an option. So if I need to email someone an EXE and/or DLL to use as-is out of the box, I have to do something silly like rename foo.dll to foo.dll.notactuallymalwarebutgmailthinksso before I zip it up & send it off with instructions to the recipient to remove the gratuitous file extension. Or zip the code & binaries up and rename foo.zip to foo.piz. Or post it to a scratch spot on my website and instead send someome a url to that file (setting a reminder to myself to delete said file later on once receipt has been confirmed). Or print it out as a series of 1s and 0s and mail it to them by carrier pigeon.
At this point, the honyemoon is over for me. I'm waiting to see if the benefits of using Gmail this way still outway the annoyances described here before going back to my pre-Google ways. Hopefully the kind folks at Gmail will make quirk #1 something subscribers can selectively opt into or out of. And hopefully they'll realize that quirk #2 isn't really making the internet a safer place - just more annoying.
At any rate, those things cost me time. If you were thinking of jumping into the Google pool with both feet like me, be advised that there are still a few quirks to be ironed out.
Posted
Oct 18 2005, 01:07 PM
by
mike-woodring