By Dan Kennedy • The press, politics, technology, culture and other passions

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Toward a better Gmail

It’s not Google’s fault. It’s the spammers’ fault. Nevertheless, I’ve got a pretty good idea of what Google’s top priority ought to be, and it’s not Google Buzz.

I truly love many things about Google. And its greatest gift to humankind is surely Gmail. But I have been frustrated over the past several years because I can’t use it as fully as I would like. I’ve written about this before. I think it’s important enough to all Gmail users that it’s worth writing about again.

Gmail lets you send outgoing e-mail using one of your other e-mail addresses. Within the past year, it also added a feature so that you can use a different SMTP server for outgoing mail as well. Theoretically, I should be able to have my Northeastern e-mail redirected to my Gmail account, and use Gmail to send e-mail from my NU address, officially stamped with the Northeastern SMTP server information.

The problem is that Gmail includes some code in a usually hidden part of the header that lets recipients know incoming messages aren’t “really” from NU. And some systems have been programmed to see such messages as spam, and either bounce them back (problem) or shoot them into the intended recipient’s spam folder, perhaps never to be seen again (bigger problem).

My solution in recent months has been to receive my NU mail and my personal Gmail messages via Apple Mail. Both are IMAP accounts, and I can move messages into Gmail folders within Apple Mail. It can be painfully slow, because even though it looks like I’m simply transferring messages into folders, I’m actually uploading them onto Google’s servers. (The advantage to this is that I can go to Gmail and use its superior search functions.)

There’s also no visual interface as good as Gmail’s, and I find that it’s easier to miss messages when I’m looking at them in Apple Mail or any other program — most definitely including Thunderbird, which is too kludgy for heavy use.

Over the past two weeks, I got brave and gingerly dipped my toe back into the Gmail waters. Then, today, a message was rejected by the Barracuda anti-spam system at WGBH. Like most of us, I just can’t take the chance that my e-mail won’t arrive. So it’s back to Apple Mail. (Or — shudder — Microsoft Entourage, whose interface looks remarkably like a Rube Goldberg flow chart.)

Now, I’m not suggesting that Google alter its header information. For all I know, it would be illegal. But surely there must be some way of working with the major security systems and coming up with a solution. Perhaps it would be possible to register with some sort of service stamping users as legitimate. I don’t know. But Google has a stake in getting this right.

As it stands, I’m working less efficiently than I’d like. And I’m costing Google money, because I’m not looking at its ads.

One giant step for Googlekind

Gmail has finally tweaked its system so that you can send an e-mail to someone using your non-Gmail address and not have Gmail information show up anywhere in your header.

Farhad Manjoo, writing for New York Times Bits, makes it sound merely like a matter of workplace protocol, but there’s more to it than that. If you send an e-mail that appears to be from one of your non-Gmail accounts, but Gmail data still show up in your header, you will occasionally find that the person on the receiving end never sees it, as it gets caught in a spam filter.

That happened to me earlier this year. Because I couldn’t take the chance that people wouldn’t receive messages sent from my Northeastern address, I actually gave up on the Web version of Gmail for a few months, futzing instead with Apple Mail. The horror.

I went back recently after being assured by Northeastern’s IT folks that the the spam problem I had described was probably a random event. But I followed the Gmail instructions this morning the moment I read about them. Given that was by far my biggest complaint about Gmail, I am a very happy customer right now.

Next up: Figuring out how I can send outgoing mail from my new BlackBerry using either my personal or my Northeastern address. Given that all my mail goes to the same Gmail account, I’m not sure I can do that. Any thoughts?

Gmail and its discontents (II)

Problem solved, although not the way I would have liked. I’m now using Apple Mail to pull in my Northeastern mail (via POP) and Gmail (via IMAP) separately. I’m able to use Northeastern’s SMTP server off-campus as well as on. So all of my outgoing NU mail contains official-looking header information, and will thus not be intercepted by anyone’s spam filter.

Oh, well. Apple Mail’s not so bad, I suppose.

Gmail and its discontents

It must be the season of technical difficulties.

I use Gmail for everything. I’ve set it up to pull in my Northeastern e-mail, and I have an alias that allows me to send mail via Gmail as if it were coming from my Northeastern address. Gmail isn’t perfect, but it’s better than anything else.

Today, though, I sent an e-mail to a colleague at Northeastern. It never arrived. I tried again. No luck. Finally, I sent the same message using my Gmail address. Bingo — she got it immediately.

What I had run into, I strongly suspect, was a hyperactive spam filter at her end. The filter saw that my incoming e-mail address did not match the underlying Gmail information in the header and flagged it as spam. (The theory is that I must have been faking my outgoing e-mail address, and so therefore was up to no good.) I’ve run into this very occasionally before, but not quite so directly.

Now, of course, I’m wondering how many other e-mails I’ve sent to people at Northeastern that never arrived. I’ve contacted the IT folks to see if there might be a solution that doesn’t force me either to stop using my NU address (unprofessional) or abandon Gmail for NU business (undesirable). But I’m not holding out a whole lot of hope.

Any thoughts?

Tweaking Gmail with IMAP

It’s tech week at Media Nation. Fresh from foisting my video issues on you, I thought I’d give an update on my ongoing efforts to make Gmail dance to my tune.

Taking some excellent advice from a few astute readers, I set up Apple Mail to engage in two-way communication with Gmail via IMAP. As promised, this proved to be a far better set-up than accessing Gmail via POP. With IMAP, Apple Mail is more or less in constant contact with Gmail, syncing messages and folders so that what’s on my hard drive is exactly the same as what’s in my Gmail account.

One thing that surprised me after I first set up Apple Mail was that copies of all my Gmail messages (and I save pretty much everything except spam) were downloaded automatically to my hard drive. I suppose that’s the idea. But what about when an iPhone user sets up IMAP communications with Gmail? Do all those messages get downloaded to the iPhone, too? That doesn’t make much sense.

Now, here’s the best part. My biggest problem with Gmail is the way it interfaces with my Northeastern account. I had set up Gmail so that it would grab my NU mail. But occasionally there are delays of an hour or more — usually not a big deal, but sometimes critical. Also, although I haven’t found any specific examples for a while, I swear that there were occasions when important NU mail never made it to Gmail.

So, I reconfigured Gmail to stop receiving NU mail, and then set up a separate Northeastern account in Apple Mail using POP (no IMAP available). Now all my NU mail is downloaded directly to my hard drive, bypassing Gmail completely. And once I’ve got it, I can move it into Apple Mail folders that are then synced to Gmail and its labeling system. It gives me all the advantages of Gmail with none of the disadvantages.

I had hoped to be able to sync Gmail Contacts with my Apple Address Book. But to do that, you need an iPhone or an iPod Touch, or a willingness to hack your Mac. Fortunately, it was simple to export my Gmail Contacts as vCards and then import them into Address Book.

All of which means that I’ve attained e-mail nirvana, right? Well, not quite. Here are some issues that probably can’t be solved, and that I’m trying to decide whether I can live with or not:

  • Cloud computing is better than desktop computing. The single best thing about Gmail is that you’re doing everything on Google’s servers. You don’t have to worry about which computer you’re working on. And you don’t have to have a bunch of different programs open. I’ve now got Apple Mail and Address Book running pretty much all the time, and that’s on top of Firefox, NewsFire, Word and whatever else I’ve got running.
  • Gmail is more aesthetically pleasing than Apple Mail. And it’s not just aesthetics. Gmail lets you compose a perfectly formatted HTML message. Apple Mail is stuck in RTF, even though it seems perfectly capable of reading HTML. I often find myself switching to Gmail to compose, secure in the knowledge that IMAP will bring everything back together in the end.
  • Labels are better than folders. Apple Mail uses folders. Gmail uses labels. IMAP makes a seamless transition from folders to labels. But, in Gmail, you can assign more than one label to a message. You can’t do that with folders.
  • No more Gmail Chat. Not unless I fire up Gmail. I don’t use it that much anyway, but I like to know it’s there.

What’s my bottom line? I haven’t quite decided yet. In a perfect world, I would stick with Gmail on the Web, but my Northeastern account is enough of a complicating factor that a hybrid solution probably makes more sense.

One thing I have not yet done is take up another reader’s suggestion and take Mailplane for a test drive. I did poke around the site a little bit, and I’m not sure it would make my life any easier. If anyone has tried it, I’d be interested to know what you think.

For that clean, squeaky Gmail Soap feeling, click here.

Gmail aliases

As I vowed, I’ve started experimenting with different mail systems. Right now I’m playing with Apple Mail, Gmail and IMAP. Unfortunately, I’ve found that when I send a message using my Northeastern address, the receiver still has my Gmail address sprinkled throughout the header, since I’m using the Gmail SMTP server. So there’s still a good chance that some of my intended recipients will see my messages as spam. Hmmm.

Gmail, heal thyself

Gmail bounced back a lot more quickly than the threatened 24 hours, I’m pleased to report. But I’ve been pondering the possibility of changing the way I use it, and this gives me additional impetus. I know there are some Media Nation readers who love this stuff, so they’ll indulge me, and perhaps provide some advice. The rest of you can skip this.

I made the switch to Gmail a little more than a year ago. For a while, I used it in conjunction with a POP account, but soon I switched to Web-only. Why?

  • My mail was the same wherever I was, even if I was using a different computer — including my archives and my address book, which are also in Gmail.
  • I could download my mail and send outgoing messages hassle-free even in places like public libraries, which often block POP access.
  • Gmail on the Web is just a nice online experience — the labeling, the display, the search features and the like. Aesthetics matter.

Over time, however, I’ve become frustrated. I hope to stick with Gmail in some way, mainly because it does such a good job of filtering spam. But I might change the way I use it. My complaints:

1. It does not integrate well with my non-Gmail account. I use Gmail to access my Northeastern e-mail. Theoretically, I should never have to log on to my Northeastern account. But it hasn’t worked out quite that conveniently.

For a long time, I had NU e-mail forward to Gmail. Mail arrived instantly, and life seemed to be good. But there were minor problems too arcane to mention, so I turned off forwarding and set up Gmail to grab my NU mail directly. There’s a delay that can last from a few minutes to an hour or more — usually not a problem, but occasionally a big problem.

It also seems as though, every so often, Gmail simply refuses to deliver a piece of mail on the NU server. Therefore, every day, I have to log on to my NU account separately to see whether there’s anything I missed. A waste of time, to say the least.

2. Every piece of outgoing mail is somehow stamped with my Gmail address. When I send an e-mail from Gmail using my NU address as my outgoing address, my Gmail address appears somewhere in the header as well. This is not a big deal, but I don’t like it.

3. Gmail’s advertising sometimes sets off spam filters. I have sent messages from Gmail using my NU address that have been marked as spam on the receiving end. In attempting to troubleshoot this, all we could think of was that Google’s ads rang the alarm.

Now, I could go back to using Gmail with POP — or, even better, IMAP. But there are some really nice features I would lose. My Gmail address book cannot easily be exported to Apple’s Address Book. The biggest sacrifice is that I’d no longer be archiving my mail on Google’s servers unless I set things up to make a separate, time-consuming operation out of it. I love the labeling feature and I love the super-fast searching, and I don’t want to give those up.

If there’s anything I’m saying that shows my ignorance, please enlighten me. I’d love to be able to improve my Gmail experience without giving up what I like.

Gmail woes

I’m increasingly disenchanted with Gmail. And it just got worse. Here’s a message I received a little while ago:

This account has been locked down due to unusual account activity. It may take up to 24 hours for you to regain access.

Unusual account activity includes, but is not limited to:

  1. Receiving, deleting, or downloading large amounts of mail via POP in a short period of time.
  2. Sending a large number of undeliverable messages (messages that bounce back).
  3. Using file-sharing or file-storage software, browser extensions, or third party software that automatically logs in to your account.
  4. Leaving multiple instances of your Gmail account open.
  5. Browser-related issues.

Please note that if you find your browser continually reloading while attempting to access your Inbox, it’s probably a browser issue, and it may be necessary to clear your browser’s cache and cookies.

If you feel that you have been using your Gmail account according to the Gmail Terms of Use, you can troubleshoot your problem by clicking here.

I’m probably in trouble over #4. I am a heavy e-mail user — especially so today, as I am doing some heavy multi-tasking while working on a story. I make no apologies, and I’m not going try to troubleshoot my problem. At least not at the moment.

E-mail request

OK, here’s the latest. I have come to the sad conclusion that I may have to phase out my longtime personal e-mail address, dan {at} dankennedy {dot} net. I’m receiving hundreds of spam e-mails a day, and just under 95 percent of them are associated with that address. It’s been hopelessly compromised after years of being out there on the open Net.

The problem wasn’t with Gmail. The problem was that Gmail’s spam filter was being forced to more than it should.

Perhaps I’ll find a way to revive it. For the time being, though, I suggest that if you want to reach me, you do so through my Northeastern account, listed in the right-hand column of this blog. Most of you are already doing that anyway.

E-mail update

I think most of my problems stem from the fact that my personal e-mail address, dan {at} dankennedy {dot} net, has become so compromised over the years that it’s practically useless. I’ve been isolating those messages at the source, and it seems like there’s two or three good messages for every 300 spam messages. Worst of all, robots have grabbed hold of it and are using it to try to spread spam to the four corners of the earth.

My Northeastern address, da {dot} kennedy {at} neu {dot} edu, seems to be relatively unharmed, as does my actual Gmail address, which I try not to use.

Occasionally I’ve seen services that allow you to set up the Berlin Wall of spam blocks: If someone isn’t already in your address book, he can’t get through unless he answers a question or fills out a form or something. Does anyone have any experience with that?

Although even if I set up such a trap for my personal address, it presumably wouldn’t do anything to stop it from being used as an outgoing address by spammers.

Thoughts?

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