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I buy quite a few apps on my iPhone, but as of late I am noticing a weird issue: any app that cost money, 'times out' after a few days use. 'Timed out' apps don't appear on my iTunes purchases history, and I am forced to buy them again(?) and re-download them before I can use them again. When the app 'times out', the icon remains, but the app immediately exits when pressing on the icon. It seems as though my iPhone may have lost the connection to the store somehow? Any ideas?

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Which apps in particular? This sounds more like a buggy app. –  Gerry Feb 21 '12 at 14:52
    
@Gerry As I stated above, this is occuring for all apps purchased on the phone, so I very much doubt that it is buggy apps. –  joshnh Feb 22 '12 at 6:37
    
I very much doubt they are timing out either. Did you jailbreak the iPhone, or anything else particular? –  Gerry Feb 22 '12 at 8:26
    
The phone is running iOS, I haven't tampered with the hardware or software in any manner. –  joshnh Feb 24 '12 at 4:57
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I'm not sure what your problem is, but iOS apps do not ever "time out". Apple specifically does not allow any app to do this, and they punish any developer who is caught doing so. The apps are probably crashing, if you don't know how to view the crash log (google it) then you should contact Apple or the third party developer asking for support (any paid app should have pretty good tech support) –  Abhi Beckert Feb 26 '12 at 1:09
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4 Answers

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It sounds like your iOS software is corrupted. I would back up your iPhone to iTunes or iCloud, follow these instructions to enter your phone into DFU mode, download the newest iOS version, and restore your iPhone with the newest iOS version. Contact iTunes support and get your purchase issues resolved. Let me know in comments if you have any questions!

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Does your trouble still appear if you purchase and download the apps through iTunes on your Mac/PC, sync the apps to your phone, and then run the apps on the iPhone?

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No it doesn't. It only occurs for paid apps purchased on the iPhone. –  joshnh Mar 1 '12 at 6:30
    
This now sounds identical to what happened in my case. When an app wouldn't run after purchasing on the iPhone, I'd uninstall it, then do a hard reset by simultaneously pressing the Sleep/Wake button and the Home button at the same time for at least 10 seconds until the Apple logo appears. Then reinstall. You may consider doing this for a new app purchase to see if it works for you before going back to your previous "purchases" and to prevent any double-charging/duplicate purchasing. If you do get stuck with a double-charge, Apple is very good with correcting your account for the trouble. –  Francis Mar 2 '12 at 21:44
    
NB doing a hard reset, if you're unfamiliar and as brutal as it may sound, does NOT erase your phone's data. –  Francis Mar 2 '12 at 21:46
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It does indeed sound like buggy Apps. Sometimes I notice newly installed Apps are more reliable after powering the iOS device off and on again. I may just be making that up, of course. I have no proof.

If your iOS needs reinstalling, I recommend iTunes: Backing up, updating, and restoring iOS software as an easy alternative to the sometimes finicky DFU route.

In addition, if you re-download an App you deleted (or otherwise went missing), you will not be charged again. Does the App Store button next to your errant App say "Install" or show the price?

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The App Store shows the price, however, I am only ever charged once. –  joshnh Mar 1 '12 at 6:29
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IMHO, the better you can do is to see this webpage:
iOS: Troubleshooting applications purchased from the App Store

If it can't help you, you can report an issue as described here:
How to report an issue with Your iTunes Store purchase

Whenever I had a problem and I reported in this way, Apple has always been very responsive, always solving my issue.

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