Evolution of Webmail

I’ve always regarded webmail as a “last resort” — something to use when you don’t have the option to configure a mail client. Even if I’ve only got 15 minutes of email to do on a strange machine, I’m more likely to spend the 30 seconds it takes to configure an IMAP account than I am to mess with webmail. I hate it that much. But one thing I’ve learned running a hosting business is that I don’t have a lot of company in this department. I keep encountering power users who depend on GMail, Yahoo, etc. It used to surprise me, but I’ve been paying more attention to the options lately.

Sure I can see the advantages of webmail systems, but in my mind, the downside outweighs the upside. I work with a lot of mail, and tend to flip it all over the place – grab 10 non-contiguous messages at a time and drag them to a folder or delete them. Sort via column headers. Forward entire threads as a single message. Mark with colored labels. Set up rules and filters for custom handling, etc. Most webmail systems either don’t support those activities or make them very cumbersome. I hate not having a preview pane, and I really hate that hitting reply always quotes the entire message, not just the bit I’ve selected. Webmail address books tend to suck, and lack integration with the OS. I could go on.

But webmail has changed a lot in the past few years. GMail’s integrated search — and accompanying dismissal of folder-ization — has a lot going for it. But more interesting to me is the Ajax-ification of webmail we’re seeing in webmail clients like Roundcube (which Birdhouse now provides). Suddenly it’s possible to select non-contiguous messages with Cmd-click or Shift-click and drag them into folders, or delete — a huge step forward for webmail. A few days ago, Apple released a new version of .Mac webmail, which takes some of the basic ideas of Roundcube and pushes them to the next level, emulating the Mail.app experience almost completely (it even has a preview pane). However, .Mac webmail still insists on quoting the entirety of a message, rather than just the selected part (I wonder how much webmail as a whole contributes to gross over-quoting?) But webmail is definitely getting more usable than it used to be.

Ajax is quickly enabling web-based apps to emulate the full power of desktop applications. The responsiveness isn’t quite there, but the feature set is catching up. If the trend continues, I can imagine myself spending more time in webmail before long, though I still like the idea of having a master repository on a drive I control.

Webmail: Love it or hate it?

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Music: Clem Snide :: Joan Jett Of Arc

21 Replies to “Evolution of Webmail”

  1. I use Gmail exclusively – mainly because most of the time I access a machine it is a pool machine, and I don’t have any email client on there.

    I used to use Mail.app from home, and Gmail from work, but since I got ADSL, it’s almost as quick to use Gmail as Mail.app. Sometimes quicker, as I generally already have Firefox open.

    My only hassle is that I can’t have my address book synched, that would be cool. I’m looking forward to that, and the ability to sync calendars with gCal/iCal (then I can also sync to my Palm).

  2. I use Gmail so I can access my mail from work (and any other computer) and the search is really helpful. I also POP my mail into Mail.app which grabs my Gmail stuff and also my ISP email address (which some people still use).

    Part of the reason I stick with Mail.app is simply because I enjoy using the Mac more than I like using Google apps. This is also why I am dying for a sync application between GCal and iCal.

  3. Andrew – What is it about being at work that prompts you to use webmail rather than configure a POP or IMAP client? That’s the second time I’ve heard someone say that in two days.

  4. since I got ADSL, it’s almost as quick to use Gmail as Mail.app. Sometimes quicker, as I generally already have Firefox open.

    Matthew, this is interesting. Do you only mean that you can get to your mail as quickly, or do you mean that you can work with your mail as quickly? The former I agree with, but to me, working with mail on the web is such a non-fluid experience that it doesn’t *feel* quick.

  5. I’ve used Gmail as my main email for a while now. Before I started favoring it I made sure I configured POP access so that I’d always have copies of my messages (both sent and received, conveniently) sitting on my Thunderbird client at home as a backup/reference. I’m firewalled at work, so Gmail’s accessibility, convenience, and utility makes for a great all-purpose inbox. And their spam filtering is better than my ISP’s (Comcast).

  6. aharden – By “firewalled at work” do you mean you have no access through port 110 or through any other common POP or IMAP port? So how do you check your work mail? What in the *world* do organizations think they’re gaining security-wise by doing things like this? Baffling.

  7. I think I mentioned this to you a while back. I use GMail in conjunction with Apple Mail/POP3 and my personal domain/address. Thanks to Birdhouse’s cPanel tools, I can have a copy of every email that comes to my personal address sent to my GMail account. Google in turn lets me link my personal address to my GMail account so that when I reply to or send an email via GMail, it looks like it’s coming from my personal address. Furthermore, I BCC myself on most emails I send from Apple Mail, so those too are copied to GMail. What this offers me is a hybrid IMAP/off-site backup with a great interface. When I’m at work and need to refer back to a thread from six months ago, I can access it via GMail. My GMail account currently has 513MB of mail–this would have filled up my server allotment if handled via IMAP.

    It has other benefits as well. GMail offers sophisticated filtering. This is good of course for filing newsletters and whatnot, but I can also ask it to forward specific emails to say, my cell phone. Then there’s Google Calendar, Reader, Chat… It’s all quite handy.

  8. Yep, no POP/IMAP access to work email. I have to VPN in to check. I suppose this is the way it is at large companies; they secure the perimeter because there’s too many darn systems on the inside.

  9. >>>
    What in the *world* do organizations think they’re gaining security-wise by doing things like this? Baffling.. i edit out junk in hte reply (if i feel so inclined). i’ve been conditioned by the inverse effect — having to cancel out of a reply because i forgot something (like a URL) was selected when i needed the whole reply.

    as far as other power mailing uses, i don’t use webmail for that. i just use it at work or when traveling (using someone else’s computer). and i use it at work just to give me more separation between personal/work life.

    btw – roundcube was really buggy for me, nont nearly as configurable as I’d like, and not as many features (which i’ll probaby never use) as horde. it *is* better than squirell mail though :)


  10. hey – you’re app totally scrunged my reply ! grrrr. (that’s why the first para makes no sense). f* it. no time to rewrite it :(

  11. Re: Draconian, I was responding to aharden there, not to baald.

    baald: No, roundcube doesn’t have as many features as Squirrel or Horde, but it isn’t missing anything I need, and I love its clean UI and superior ability to manipulate large message sets (e.g. arbitrary selections, drag and drop).

  12. oh – i have to vpn in also to use a client for work mail, though we have web access without vpn.

  13. part of what i said in my munged reply: all webmail clients in my experience let you do arbitrary selections. its just with checkboxes. but i just saw a firefox extension that lets you select an area and it (un)checks all boxes in that area.

    btw – the bug i was having with RC: i’d see duplicate message entries in my inbox, but could open neither entry – it would just refresh the mailbox. frustrating to say the least.

  14. Yes, I know all webmail clients allow checkbox multi-select, but that’s exactly the kind of thing I’m talking about when I say I consider most webmail systems unusable. That’s a UE slowdown that just grates on me no end.

    I think I’ve seen that duplicate entry in RC issue before….

  15. heh. all i have to do is select “check all” and deselect the 1 or 2 messages out of the hundred on the screen that aren’t spam ;)
    guess that’s why it doesn’t bother me as much

  16. Well here’s another draconian situation. My work also only allows the WWW (ports 80 and 443) through the firewall. You can also get limited telnet and ftp access, but you have to be on the “Internet” team and have an acct on a server with an external interface.

    So it’s GMail for me :) (well, OK…I also proxy ssh out port 80 on our WWW gateway so I can connect to birdhouse hosting :)

  17. Telnet and ftp? Not ssh and sftp? So they clamp down all the ports and then let their own tech staff send passwords all over the wire unencrypted? Smaarrrrttt.

    The other thing I don’t understand is that orgs allow use of webmail. Isn’t the whole point of closing port 110 to prevent people from doing personal email at work?

  18. I don’t trust email on my computer. Web based mail scans it when you read it. You only download if you look at it and even than the site will tell you “Don’t trust this one” So it’s harder to get viruses from email this way. I have three webmail address i use. For different kinds of mail. Plus i don’t want my computer filled with that junk. good luck with that.

  19. Rachel – Web based email does not provide any inherent protection against viruses over desktop mail clients. If your desktop mail client can’t do that, it sounds like you’re using a 10-year-old email app or something.

    Bigger picture: The solution to the virus problem is really, really easy: Get a Mac. There is absolutely no good reason to still be running Windows in this day and age.

  20. When less is more – playground scale.

    It is kind of funny anachronic experience: I came to like webmail back in 1999, and it was http://www.Email.cz, czech web-email service effectively started as a small company by a devoted IT geek.

    It had lots of side-features no other free-webmail had at the time (hotmail? shockingly bad workflow hell until 2007!), the author listened to users and was implementing changes regularly. Filtering, SMS notices, backups, fav/recent contacts, templates… useful tools and details.
    Because the internet “community” was not yet that massive and fiven czech republic population scale it was manageable.
    And without corporation board there was room for experiments. And maybe czech developers tend to have an eye for detail and rigorous solutions.

    Then Email.cz it was bought by a major national web-portal company Seznam.cz and merged with their good but rather boring “gmail” style webmail.

    Often the interesting, inspiring stuff happens somewhere in a corner without much notice, to be beaten by the rumble at the main table. Only between courses some start looking around…

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