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Why I Don’t Webmail

I’ve never liked webmail. I’ve always looked at it as a hack to get around the rules of your over-bearing corporate IT department. Many of my friends consider Gmail’s web interface to be the ultimate email application. While I do applaud Google’s innovation, I prefer Apple Mail. This is why.

Over the past few weeks, there has been a noticeable increase of complaining, praising, and/or defending of email clients in my circles at the office, home, and the portion of the web that I follow. I have been using email in one form or another since 1992. In my experience, I have learned that no two people use email in entirely the same way and it is therefore very useful to share your techniques whenever possible. It is in this spirit I want to share why I prefer a stand-alone email client to webmail—specifically, why I prefer Apple Mail to Gmail’s web interface.

Multiple Email Accounts

I have eleven email accounts (working three jobs and playing in three bands has its down sides), three computers and an iPhone. Most of my accounts are Gmail based, with the exception of Mobile Me, Yahoo, Hotmail and AOL accounts which I use for testing email marketing campaigns.

I use Apple Mail to manage all of my email accounts via IMAP where possible. This ensures all my email is consistently synced on all my devices. Apple Mail allows me to view all of my messages from all my accounts inline and threaded by conversation in a single inbox, and it is smart enough to know to reply using the account (and corresponding signature) the message was sent to.

Gmail’s Mail Fetcher allows you to access up to five other email accounts. Five email accounts isn't enough for me.


Apple Mail allows me to drag attachments into the message I am composing. No form widgets to click. No need to browse my computer through. I can drag any file into the body of an email to attach it, or I can drag any file onto the Mail icon in my dock to create a new message with that file as the attachment. If you do use the file browser, the OS X file browser is iLife aware, making it easy to find anything in any of your media libraries. 

If you use Gmail with a WebKit browser, you can drag attachments onto a file upload form button, but in Gmail, you must first compose a new message, and click the Add Attachment link to display this form widget.

Searching and Filtering

Google is king of searching, but Apple Mail does boolean searches, too. The syntax is different but I have found them to be on par as far as results go. Where Apple Mail outshines Gmail’s is its filter-as-you-type method. This makes it easier to catch typos or make corrections as you go. You also have the option of saving your search as a smart mailbox. While Gmail’s UI allows you to create filters based on search criteria, if you decide to save a search after the fact, you have to go to the filter screen and recreate it.

Apple Mail is also indexed system wide on Mac OS X. Spotlight searches in OS X return Mail and Address Book results. Being able to find email messages based on text layers of Photoshop files in email attachments has saved my ass on more than a few occasions.

Data Detectors

Data detectors in Apple Mail provide context menus for addresses, phone numbers, dates, AIM names, etc. allowing you to create or add to existing contacts, create calendar events, and display maps. Gmail’s UI, as far as I can tell, provides nothing like this.

User Interface

I find just about everything to come out of Google extremely difficult to look at. For something I use as often as email, homeliness is not acceptable. But let’s put esthetics aside and cut to the chase. The thing that sets Gmail’s web interface apart from every other email client is the way it handles threading, or as Google calls it, "conversations."

As an old school email guy, the trend of top replying to emails deeply irritates me. Google has done a wonderful thing by forcing normal people into a more traditional bottom reply model. Not only this, but their implementation also automatically threads email exchanges. You’d think for this reason alone I would be a die hard Gmail advocate.

The fact is that “bottom reply” isn’t actually the ideal alternative to “top reply.” Gmail masks top-reply messages into a top-to-bottom stacked conversation. The ideal alternative to top reply is to only include specific text of the conversation in the body of your reply only if it is explicitly relevant to something you are referring to, and to only include the relevant portion of text.

I believe Gmail approximates this model as closely as possible in this top-reply society. Sadly, neither Gmail nor Apple Mail have an ideal implementation. Gmail has no way of replying to an email while only including selected text. Apple Mail does this, but automatically places it below the insertion point. Thankfully, John Gruber has written an Apple Script that automates this process.

I realize that no matter how long I scream and cry for people to adopt traditional email syntax, it simply is not going to happen. In this case, Gmail’s solution is the most innovative, and I applaud Google for being the only email innovators currently out there. However, I prefer having more control over the emails I send, and Apple Mail lets me do this while still threading by conversation.

Speaking of threading, the Gmail inbox is sorted in descending order with the most recent conversations on top, but the conversations themselves are in ascending order. I find this inconsistency annoying. Apple Mail lets you sort in ascending or descending order and this order is respected in thread view.

While Gmail’s interface is elegant in theory, it’s execution is terrible. This is where esthetics comeback into play for me. There is entirely too much going on on screen. There are too many colors, font sizes, weights and widgets crammed into the view, and way too little whitespace. I have a lot going on on my workstation; Two displays, six virtual desktops, and way too many windows to deal with. Keeping an organized, easy to use workspace is critical to my sanity.

In Conclusion

Excessive visual clutter, lack of drag-and-drop, limited search, and support for only five email accounts all combine to form one huge deal breaker for me. Even if these elements were addressed, I still don’t know if I could bring myself to manage email through a web based client. It just feels hacky, and I say this as a web application developer.

The future of computing is in “the cloud,” but I believe that is where the data should live, not the interface. Hopefully there is a Cocoa programmer out there somewhere who gets the importance of top-reply, threading, IMAP, plain text and rich HTML email, and doesn’t care about the nearly non-existent market for creating a proper email tool ... for me.