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iPhone 3G Owners, Beware The New 3.1 OS Upgrade

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If you're a gadgetophile like me, you love firmware updates because it's like giving your smartphone, camera, or other mp3 player a mini-makeover. If you're normal, however, don't rush into it—the best thing to do is wait a bit and see what problems are reported from the front line. Take for instance this issue between 3G iPhones and Exchange servers, which no longer play well with each other after yesterday's 3.1 iPhone OS upgrade.

According to this Apple user forum discussion, if your company's Exchange server has encryption enabled on its ActiveSync settings, then anyone with the 3G model running the new 3.1 OS will find that they can no longer connect. Instead they get this error message: "The account '——-' requires encryption which is not supported on this iPhone."

Hopefully Apple will release an update to the update shortly, or your company's IT department will get all "who cares" about security and turn off encryption. In the meantime, clutch your phone dearly and keep away from any OS improvements until at least a few days have passed to reveal any hidden problems.

"iPhone 3.1 Won't Sync w/ Exchange" [Apple Support Discussions] (Thanks to Casey!)
(Photo: thms.nl)

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Or your IT department will get all "Sorry your unsupported phone doesn't work. Why don't you use the corporate standard and get yourself a Blackberry? I hear they've had copy and paste for over a decade now!"

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I'd go as far to say:

If you have any sort of device (computer, smartphone, GPS, etc) that you require for work - ALWAYS wait before upgrading any aspect of it until you hear/read that it won't break the functions you need.

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Oops. That'll teach me to update right away. I guess that means it's time for a fun conversation with IT.

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Funny, my exchange server is still working fine. In fact, my company is now allowing people to get iPhones instead of BlackBerrys

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The rule was never to install Microsoft software until Service Pack 2. Looks like Apple is following in those footsteps.

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@shepd: *shrug* My company supports both kinds of phones, unofficially, because the IT guys all have iPhones.

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Luckily I don't use Exchange! i upgraded right after it came out...

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Thank goodness I haven't upgraded yet.

Breaking SSL connectivity for the Exchange client was just friggin stupid. Doesn't Apple test that kind of basic functionality?

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I don't have an Iphone, but I have a 32gig Ipod touch and I was about to upgrade to 3.1 last night.. but when I plugged in my Ipod it started to "sync" which included "Back up Ipod" and it was slower than a typical windows Defrag. I left it plugged in a couple of hours and the progress bar was less than a 1/4th along..


I'm not sure if this is normal or not.. but I gave up on it and went to bed.. I'm going to try again this afternoon when I get home. I might even time how long it takes to get to the end.. if it ever does.


When 3.0 came out I was VERY irritated that it came with a 10 dollar price to upgrade. I have never had to pay for Ipod upgrades before, so I had no idea that they charged for it. I didn't upgrade then because I think that price is too high, but now the 3.1 upgrade is only 4.95, which I think is more reasonable. I still think it should be more heavily advertised that the upgrades cost money though. I've been an Ipod user since the first Nano and never had to pay to upgrade until now.

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My alarm on the iphone didn't go off today... I updated the firmware on my 3gs last night. Coincidence?

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I upgraded last night, and I'm having no connectivity problems with my Exchange server. And yes, SSL is on.


My Exchange server is 2003, maybe the problem is specific to Exchange 2007?

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Why don't companies like apple test their updates before releasing them.

I know that theres no way to release perfect code but if your making a update for some software, you at least want to properly test every feature you made changes on.

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@Kimaroo - 20% More Kitty Added!: It's only $5 now? Aargh, I finally gave in and paid $10 for the 3.0 update 2 weeks ago because a lot of apps I wanted to download were 3.0 only.

Also, the upgrade to 3.1 last night went very slow for me, and even this morning when I tried to sync it got stuck in "Verifying iPod" for 20 minutes before I just had to unplug it and go to work.

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There is another possibility that hasn't been considered: The error is about "encryption which is not supported", which could be a complaint about using weak or deprecated encryption.

I know for a fact Google's Exchange sync for Contacts/Calendars uses 128-bit so that IS supported. If ActiveSync is like most other MS protocols, 40- and 56-bit is also possible, but definitely not recommended, and the iPhone might be flat-out refusing to use 40-bit or something.

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I upgraded my iphone OS without any problems. I don't use exchange, though.

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@shepd: My wife talked to the company that they outsource their IT to before she got an iPhone and they said Heck yeah, it works better than Windows Mobile, and Blackberry when syncing with their servers. She was able to configure the phone herself in about 5 minutes. She never did tell corporate management that she dumped her Windows Mobile device and got an iPhone.

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@Kimaroo - 20% More Kitty Added!: Some experts in the tech industry have said that they are charging for the iPod Touck upgrades to comply with Sarbanes-Oxley. I don't fully understand the rationalle or reasoning behind the charge, and why some updates are free, and others are charged, and why the fee is only on the Touch.

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@Coyote: I stand corrected. This has nothing to do with SSL, but with encrypting the data at rest on the phone. Only the 3GS can do that. Before 3.1, older iPhones would say they could do it even when they couldn't.

So yeah, it's now working as designed, vs. cheating and leaving your corporate email unsecured.

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@Neophiliack: Yep.. I was thinking about it recently for the reason you said, because of the apps.


It's very annoying. And people say that Macs don't screw you around..

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@Razor512: They do, but you can't duplicate EVERY circumstance under every situation.

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@durkzilla: Don't think so. We use a 2007 server and it's still working for me.

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I use Exchange 2007 with SSL, Contact, Mail, and Calendars. No problems with iPhone OS 3.1 this morning.

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Apple issued an updater to iTunes which erased/reformatted any mounted drive whose name started with/contained a "space". Immediately after wards, people were having their drives wiped, so they pulled the upgrade. After that incident, I started to wait around a week before applying any upgrades, and also re-run the check upgrades feature to make sure the upgrade wasn't pulled/supplemented. It already happened once with a Java update they pulled two days after they released it, so I think it has helped me. Except for virii/malware definition updates, I think no harm can come from waiting like that.

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@GitEmSteveDave_IsPyroclastic: I should mention this was MANY years ago with the iTunes thing, and was with vers. 2. [www.xlr8yourmac.com]

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@shepd: "I hear they've had copy and paste for over a decade now!"

Both the iPhone & Blackberry have copy & paste regardless of this update.
Arguing which device has had the feature longer is irrelevant.
In fact, doing so is tantamount to the idiots who post "FIRST!" on message-boards.

I'd seriously hope no IT department is basing their smart-phone recommendations on copy/paste implementation date.

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@SgtBeavis: Of course not! You don't think they test their own stuff for downrev incompatibilities like they forced their iPhone app developers to do, do you? This just means you need to upgrade your lowly 3G to a less-obsolete 3GS.

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@shepd: And iPhone has copy and paste now. That horse? Beaten and dead.

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@GearheadGeek: Yeah i'm getting the feeling at this point they consider it a favor if the new OS updates work at all on the 3G and orignial iPhones. Since 3.0 came out those of us without a 3Gs have suffered horrible slowness, it doesn't appear they're addressing this issue as two subsequent release have done nothing at all but update iTunes or 3Gs features.

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Upgrade, bah I want to downgrade back to 2.2, on 3.1.0 my text messages take over 20 seconds to open now. I even cleared out my entire history so there are only like 2 messages, it helped a tiny bit.

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@Coyote: Good info. So, can you confirm that the 3.1 update is working correctly with the version of Exchange that powers Google Sync?

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@Razor512: You would be amazed how a change in a seemingly isolated part of the code can manage to mess up something seemingly unrelated. There may not have been a change to the exchange code at all. Now that I'm done being the devil's advocate, it seems like a very in debt full testing of the product would be done before a big release like this, and testing it against secured exchange would definitely be something I would do as part of that test.

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@Rachacha: If it's to make good with some weird law then why not just charge 99 cents? Why 10 dollars or 5 dollars?


If I had known that the updates would be this costly I would have thought twice before deciding that I wanted an Ipod Touch. I could have bought an unlocked smartphone with wifi for less than what it cost at the time.. It wouldn't have had as much storage space, but the updates would be free. As they should be.

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@MMD: It's still fun to reminisce about how that beaten and dead horse also arrived a couple years late to the race.

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Looks like it works for the iPhone 3GS phone, it's the older 3G's that are having problems.

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Computers don't make mistakes. What they do, they do on purpose. Right now, your information's being fed into every computer mainframe, satellite, laptop, and supermarket scanner that make up the Global conspiracy known as...The Beast.

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@shepd: We dont support blackberry OR the iPhone, only winmo 6.1/6.5. Samsung Omnia is big here, lol. Although the VPs are getting iPhone so we kinda sorta support them. Also we are locked in with Verizon for our phone service, if or when the iphone comes ill be moving to that or the Pre, But my contract is up in 20 months lol so ill have my omnia 1 for a while =(

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@H3ion: *cue the Apple fanboys screaming that Apple is still better than Windows*

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@SgtBeavis: It doesn't break SSL functionality. It breaks the requirement that mail ON THE DEVICE be encrypted. It's an optional setting in Exchange that some turn on and some turn off. It has nothing to do with SSL.

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If you don't utlize that stuff I have found that 3.1 has returned my phone back to pre-3.0 speeds with a restore and a "set up as new phone" option. You lose app data but everything else is still synced to iTunes.

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@pecan 3.14159265: The Swayz already knows your information. Chuck Norris thinks it's another fist beneath his beard, but it's just where The Swayz rests, waiting, and ever vigilant to take his rightful place in this world of mere mortals.

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@madog: He doesn't have cancer, cancer has Patrick Swayze.

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I did the upgrade last night. My iTunes had been saying "the software required for communication with iphones is not working, repair?" for a while, but I had ignored it since the iphone was still syncing just fine.

iTunes spat out an error message midway through my install, the phone was stuck in the middle of the firmware update, and I had to restore it to factory. Had to re-download all my apps.

A simple patch turned into a long night.

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My company has encryption enabled and my iphone is still syncing after upgrading to 3.1.

Could it be something else causing the issue?

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The new behavior is, in fact, a feature: iPhone 3.1 respects an exchange-server setting that requires hardware-level encryption, something that allegedly only the iPhone 3GS phones has.

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@GitEmSteveDave_TheREALChrisChan: Quicken made a similar faux pas in the past no more than 2 years ago. The update for Mac replaced user's desktop folders. Their solution? Release another update that disabled automatic updates!

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@madog: Correction, QuickBooks. Same shorty company though.

[www.macobserver.com]

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@Kimaroo - 20% More Kitty Added!: Just an update.. I plugged in my Ipod to sync and set a stopwatch at the same time.


I would say it looks about 1/3 the way done.. and the stopwatch says 3 hours and 34 minutes so far!!


At this rate it MIGHT be done by the time I'm ready for bed... Is there something wrong here? It seems wrong.