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

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.

Discover more from Media Nation

Subscribe to get the latest posts sent to your email.


Steve Kurkjian talks about his nonretirement


A big night for my old friends at the Phoenix


  1. Rich Carreiro

    I’m not sure what header info it would be. I just sent myself an email via Gmail, telling it to come from my MIT account and go to an address at my personal domain. Here are the headers (with specific email addresses redacted). Only things that mention google are the MessageId: and one received line. However, lines like that (especially the Received: line) will exist in any mail message that was sourced by a machine remote from the “home” SMTP server sending mail through the “home” SMTP server. In other words, if NU lets you use authenticated SMTP to send email through NU’s servers from your laptop when you’re in, say, Starbucks, you’ll have a similar Received: line.

    Delivered-To: XXXXXX@my.personal.domain
    Received: from (DMZ-MAILSEC-SCANNER-4.MIT.EDU
    by (Postfix) with ESMTP id AE5B5BA80E2
    for ; Wed, 10 Feb 2010 13:55:33 -0500 (EST)
    X-AuditID: 1209190f-b7bbfae0000035e9-8b-4b730116e738
    Received: from (MAILHUB-AUTH-2.MIT.EDU [])
    by (Symantec Brightmail Gateway) with SMTP
    id FC.B6.13801.611037B4; Wed, 10 Feb 2010 13:55:18 -0500 (EST)
    Received: from (OUTGOING-AUTH.MIT.EDU [])
    by (8.13.8/8.9.2) with ESMTP id o1AItHjR028838
    for ; Wed, 10 Feb 2010 13:55:18 -0500
    Received: from (
    (authenticated bits=0)
    (User authenticated as XXXXX@ATHENA.MIT.EDU)
    by (8.13.6/8.12.4) with ESMTP id o1AItYmQ006152
    (version=TLSv1/SSLv3 cipher=RC4-MD5 bits=128 verify=NOT)
    for ; Wed, 10 Feb 2010 13:55:36 -0500 (EST)
    Received: by pzk12 with SMTP id 12so352882pzk.13
    for ; Wed, 10 Feb 2010 10:55:15 -0800 (PST)
    MIME-Version: 1.0
    Received: by with SMTP id f16mr402337rva.153.1265828115792;
    10 Feb 2010 10:55:15 -0800 (PST)
    Date: Wed, 10 Feb 2010 13:55:15 -0500

    • Dan Kennedy

      @Rich: As you can see, there is Google info in the header. I’m not much of a techie, and you’re from MIT. But when I’ve discussed this with the IT people at Northeastern, they’ve told me that there is definitely a somewhat greater chance of winding up in spam if I use Gmail to send NU mail than if I do it the approved way.

      The bounceback message I got from WGBH said the problem was with my IP address. I immediately turned around and sent it via Apple Mail (presumably using the same IP address, since I didn’t go anywhere), and it zipped right through.

  2. I haven’t had a problem with messages sent using Gmail not getting through. Instead, my biggest complaint is that it sometimes takes 30-45 minutes for an email sent to one of my other accounts to arrive in Gmail. If they could speed that up I would be much happier with it.

  3. Jeffrey Cox

    I find Apple Mail to be a superior product if you have to deal with multiple email addresses. I can store and move emails to folders. I hope that Apple Mail improves searches in next release.

    With that said, is Google Buzz a Facebook killer?

Powered by WordPress & Theme by Anders Norén