The iPhone’s Mail app connects to Google Gmail — and it’s paid version, Google Accounts — via the IMAP protocol [Wikipedia link]. Until Apple and/or Google get off their duffs and provide built-in push Gmail (or absent that, Google Sync Gmail for those not otherwise using their single Exchange ActiveSync slot), IMAP is all we have. (And IMAP IDLE may be what we have for push Gmail as well…) So what’s the problem?

Gmail was born of and for the Web, and admittedly Gmail for the iPhone’s Mobile Safari web browser is among the very best WebApps on any platform. However, many people still use, and even prefer to use, local clients like the iPhone’s Mail app, and for that or any local client, Google’s IMAP implementation has always been a second-class citizen.

Forgetting for now for the mapping of labels to folders results in multiple copies of the same email being stored on the local side, one of the major issues with Google’s IMAP implementation is their ludicrous 10 simultaneous connection limit. This might not seem particularly strict, but given that every client can and does typically open multiple connections and having your iPhone, desktop, and laptop all open at the same time can cause Gmail to error out.

On a daily basis, users have to carry the mental overhead of carefully and conscientiously closing email clients on one machine before turning on another, or enabling or disabling a VPN connection (which then treats the mail client as a new set of connections).

By contrast, MobileMe and Exchange/ActiveSync have no problem with this usage pattern. Add to this random “invalid certificate”, “unable to find mailbox: inbox”, “over capacity”, and other errors, and the state of Google’s IMAP implementation is really called into question.

For iPhone Gmail users, the lack of quality error messages (likely something that needs improving on Apple’s side) makes it particularly frustrating, as many of the different problems listed above simply result in an “incorrect password” pop-up box. (See image at the top of this post).

Personally — and I’m not alone in this — I’ve pretty much abandoned front-facing Gmail. I still use the unmatched excellence of Gmail’s server-side filters, but then forward the mail itself to MobileMe. (The irony of the once-plagued MobileMe service now proving more robust over IMAP than Gmail isn’t lost on me and should be lost on Google).

For those who maintain Gmail is free and we shouldn’t complain, Google Accounts — which is paid for — exhibits the exact same problems on a regular basis.

Gmail is arguably the best webmail on the internet. It could easily be the best email period. Google’s finally taken the humorously long-standing “beta” tag off the service. It’s gone prime time. It’s time to make the IMAP implementation live up to that level of standard.

This is a story by the iPhone Blog. This feed is sponsored by The iPhone Blog Store.

Dear Google: Please Fix Gmail IMAP Problems

As opposed to “push” style ActiveSynch, MobileMe, or Yahoo! iPhone mail, traditional POP or IMAP accounts, like Gmail or ISP mail, needs to “fetch”, or check the server on a certain schedule to see if there are new messages.

Reader Mike wrote in pointing us to a thread on the Apple Discussion Forums about “fetch” email being broken with iPhone 2.1. I only fetch mail from Gmail, and Gmail IMAP is a strange and buggy implementation which gives me considerable problems beyond the iPhone, so I can’t say whether anything is really broken or not in 2.1.

Reader Steffen, however, after thinking the problem could just be undocumented IMAP IDLE behavior, decided to run some tests:

Finally, I had some time to look into this thorougly. I dumped IP traffic all night to see what iPhone does. My iPhone is set to retrieve data every hour. Here’s when the iPhone actually connected to my IMAP server:

09:36 PM, 10:44 PM, 11:02 PM, 12:36 AM, 06:36 AM, 09:38 AM, 09:45 AM, 09:57 AM

Looks like everything but an hour to me… Oh yeah, forgot to mention… I’ve turned off everything except for GSM radio do be sure to get all traffic. The last three connections occurred when I started to play around with the iPhone this morning. So, the effect that lead me to the assumption of IMAP-IDLE on the iPhone seems to be something else. It appears that the iPhone will contact IMAP more often while using it and somehow random while idling… So, no IMAP at this time, but maybe interesting as well…

Definitely interesting! Thanks Steffen!

Any other readers out there got “fetch” problems? Wacky behavior? Please let us know!

This is a story by the iPhone Blog. This feed is sponsored by The iPhone Blog Store.

Got “Fetch”? POP/IMAP Email Broken in iPhone 2.1?

Warning: We may get medium-geeky here for moment. Adjust your pocket-protectors accordingly.

Apple is using the iPhone to crack their way into the enterprise. No big surprise there. What is surprising, however, is just how Sun Tzu their being about it. How so?

Bottom line, for an end-user, the interface is the app. Sure, we recognize names like Exchange, ActiveSync, even BES, but for most typical users, firing up Outlook or switching on their Blackberry IS their email. They don’t see what’s going on programmatically behind the scenes, don’t care what protocol is hand-shaking and packetizing their data as it zips from server to server in its chaotic relay from sender to receiver. They just see their email, and they just know that it was there when they needed it.

Given that, Apple licensing Exchange ActiveSync becomes more than just interesting. Why? Because they didn’t buy Outlook. They’re making their own MobileMail app which will seamlessly handle Exchange, but, oh by the way, will also handle MobileMe (the new .Mac refresh already billed as Exchange for the rest of us), as well as the usual Gmail, Yahoo!, etc.

So, for the end user, ActiveSync disappears behind the MobileMail iPhone interface. And if they have a home account, be it MobileMe, Gmail, Yahoo!, or whatever, the differences become less and less apparent (especially as push-like technologies propagate the different services), and in the end, ActiveSync disappears and people just think of their MobileMail app.

Meanwhile, the technologies behind MobileMail, with the advent of Snow Leopard Server, get more interesting, especially with Apple offering open, standards-based protocols like IMAP IDLE, and developing and releasing to the Open Source community similar code like CalDAV for push calendar and now, CardDAV for push contacts.

All of a sudden, a business could run an Exchange-like server without any Microsoft like licensing fees (which anyone who has dealt with them can tell you are money trap unto themselves).

Most interesting of all, if a business had deployed iPhones and they decided to switch from Exchange to Snow Leopard (or any *nix server using the FOSS implementations on their own), their end users may not even notice.

Roughly Drafted has more on Snow Leopard and its possible implications for Exchange/SharePoint users.

This is a story by the iPhone Blog. This feed is sponsored by The iPhone Blog Store.

iPhone Now Even More of a Business “Trojan Horse”?

Roughly Drafted, the passionate little partisan site that could, is back with a look at why Apple would choose to license ActiveSync from Microsoft while at the same time championing more open standards like IMAP and CalDAV with Leopard Server.

Having suffered under the anti-trust encrusted fist of Microsoft previously with both Excel (originally launched on Mac) and Internet Explorer (which at one time shipped with OS X) to name but two examples of Redmond’s penchant for partnercide, Roughly Drafted explains how licensing a technology is different than licensing an an application. Namely, if you rely on a partner to deliver an application as your solution, your customers grow accustomed to and invested in that solution, and you become dependent on and, ultimately subject to, that partner (and the brutish manipulations thereof). However, if you license a technology and build your own application, your customers see only your front end and if ever a partner attempts to surreptitiously bury twelve inches of pointy steel between your shoulder blades, you can always license a competing technology — or switch the back-end to your own, already existing, technology.

In fact, as Apple develops its own Mac OS X Server integration with the iPhone, and develops tight integration with its own .Mac services on a subscription basis, it can wean iPhone users from Exchange Server toward its own products using the powerful incentive of much lower infrastructure and per user costs. However, there won’t be any customers to entice if the iPhone doesn’t first ship support for Exchange.

Having lived and worked through the rise of Internet Explorer 6 and the amazing power, convenience, security nightmare, and proprietary market-grab it created, and the even more compelling, insidious sameness of Exchange Server, I both appreciate the concepts Microsoft brought to the business table and detest the method in which they brought them. Why?

Communication needs to be free (as in freedom from single-vendor lockdowns) and small and medium sized businesses need the ability to be able to move to and from whichever service provides the best capability at the best price to suit their needs. IMAP IDLE and CalDAV may not be the solution, but they’re part of getting away from the problems of Exchange, and if the iPhone can sneak them into more IT shops, and into the mindsets of more be-fud’ed IT departments, then sneak away!

What do you think?

This is a story by the iPhone Blog. This feed is sponsored by The iPhone Blog Store.

Is ActiveSync an “Open” Apple Trojan Horse? – Wait-a-Thon

One of the most interesting stories at Macworld hasn’t gotten a lot of attention in the larger press – namely that Google was around at Macworld a lot more than most people realize. It’s not just that they have a medium-sized booth featuring both their Mac products and new iPhone-compatible web offerings. No, the real story about Google at Macworld is that it’s very clear that Google has the iPhone on their collective mind in a big, big way.

Google’s services will continue to be great on the iPhone even after their Android OS hits the market. Read on to find out why!

Google In Line for the Keynote

Michael Ducker and I covered the Macworld keynote this year¹ – we lined up at 3am and were lucky that we did – I spoke with somebody that lined up at 5am and was forced into the overflow room.

I mention this because there was a large pack of Google employees at the very front of the line. There were about 20 at a time, “working” in shifts, so that there was a grand total of around 40 or 50 employees there who came in line when the keynote started. That probably caused some grumbling amongst those in back. The Googlers went so far as to have stockpiles of pizza, coffee, and even a tent (originally three until the cops said no) for sleeping.

The interesting thing, though, as Valleywag reported, was that this was a regular and company-sponsored sort of effort, right down to Google’s Vice President, Search Products & User Experience Marissa Mayer leading the charge. What’s her explanation?

“The man gives a great presentation. Hopefully we can learn something.”

…that’s a very nice and understated way of saying something else: Google seems to have a fixation on the iPhone.

It’s not just the line at Macworld, it’s that as we waited in line a Google employee got bored and did a survey of how many people in line were using iPhones – both actively and whether or not there was one in their pocket. It’s not just the booth at Macworld where Google was showing off their new iPhone-optimized services, it’s that they come out with iPhone optimized services on a regular basis. They update these services on a regular basis. These services work really well on the iPhone.

Case in point: Gmail, more specifically Gmail’s new IMAP service. I’ve used Gmail with a browser on my desktop, with Mail.app, with Thunderbird, with Outlook, with Windows Mobile Outlook, Versamail on PalmOS, and a few others. I’m not exaggerating when I say that no client, desktop or otherwise, does Gmail IMAP better than the iPhone. I say this as a person who generally thinks the the iPhone’s email client sucks. But every other client has bogged down or otherwise acted weird with Gmail’s IMAP. Not so with the iPhone, it’s as good as email gets on the iPhone. That’s either serendipity or Google thinking very seriously about the email client on the iPhone when they designed their (quirky) IMAP implementation.

…A popular phrase among developers (especially, believe it or not, among Windows Mobile developers) is “eating your own dog food.” The idea, basically, is that if you’re working on something you need to use it. It seems pretty clear to me that there is a large portion of Google employees who are eating the iPhone-brand of dog food. I’m guessing that Google’s apps rock on the iPhone because they want those apps to rock on the iPhone because they use them on the iPhone.

Android

Which leads us to Android, Google’s upcoming Smartphone Operating System. We here at Phone different never really believed that Android would compete directly with the iPhone and the more I hear about Android the more I think it’s aimed at a broader (read: cheaper) market. Back in November, Mike wrote:

Google’s use of webkit as the browser on Android reinforces Apple, and by the time Android phones are actually released, iPhones will be even farther ahead in terms of features — Android doesn’t even support wi-fi or bluetooth yet. It could easily be that Apple is trying to grab the high-end customers and Android is aiming for everyone else.

…While we should admit that these days the “high-end” is getting bigger and pushing more into the mass market than we may have expected, the point still stands. Google is putting development resources into quality web apps for the iPhone. Even if we grant (as we should) that development is easy for iPhone web apps, resources are resources. Yes, even for Google. Those resources, presumably, could have been redirected at Android either to make it better or to keep the iPhone from having a great Google experience.

No doubt about it, Google hearts the iPhone.

So when Steve Jobs was asked about Android, his take was almost spot-on:

“I actually think Google has achieved their goal without Android, and I now think Android hurts them more than it helps them. It’s just going to divide them and people who want to be their partners.”

There are basically two options here, and I see them as equally likely:

1. Google is trying to be the uber-service to everybody, everywhere, on every device possible. They’re a bigger giant now than even Microsoft of the 90’s and their plan for world domination includes offering great services even on “competing” devices. They will overcome the problem Jobs mentions through sheer size and resources.
2. Google does not foresee a time when Android would “divide them and people who want to be their partners” because, as far as the mobile space goes, the only thing they’re trying to win is the low-end space. They want Microsoft and Nokia’s pieces of the commodity pie, not Apple’s media-centric market.

I’ll take the easy out and suggest that it’s mostly option 1 with a side of option 2. There may be a day when Android competes directly with the iPhone and Google finds itself in the awkward place of deciding whether or not to favor one over the other. Given the timeline of Android development, though, that day is a long way off. In the meantime, it’s a safe bet that Google will continue to do a great job supporting the iPhone. And vice versa.

¹ Ducker took our photos and I gotta say I think they turned out better than most others’ (see his Macbook Air gallery, for example).

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Google’s iPhone fixation