iPhone and iTunes not syncing some photos problem

For some reason iTunes (on a Windows Vista PC, in this case) is having a problem syncing certain photos with my iPhone. I’ve created a separate iPhone folder for photos that I want to keep on the device, and filled it with 44 pictures for my test. But only 15 of the photos got transferred from the folder to the iPhone. What’s more, some of the photos that transferred are messed up, with weird errors, as shown with this one (bad resolution because I had to take it with a Nokia phone up close; I don’t have a digital camera).

Anyone else experiencing the same problem? Solutions? Comments welcome.


53 Responses to “iPhone and iTunes not syncing some photos problem”

  1.   1 Halk

    I’m having the exact same problem. I have 2 subfolders with pictures in the iPhone folder I made for picture. iTunes only transfers 1 picture from each and they are corrupted. The photos were exported at 1024×768 from Picasa.

  2.   2 JBred

    Hello Folks:
    I initially activated the iPhone on my Macbook, which went smoothly as accepted. However, I keep all my photos, music, etc primarily on the Vista machine in my study. When I went to sync with the vista machine, the same problem you are reporting — photos don’t all make it over, funny banding and corruption, iTunes somethimes hangs.

    I haven’t completely figured out the root cause, but here is a work-around:
    Use a usb drive or partition formatted in FAT32 as opposed to NTFS, and try to sync from folders on the FAT32 partition/drive. Works like a charm.

  3.   3 Scott

    Having the same issue when syncing photos from Windows Vista to iphone…extremely frustrating. I’m going to try the workaround through a FAT32 drive and see if that works. Hopefully this can be fixed with firmware.

    How do you report this problem to Apple?

  4.   4 Josh

    I thought I was the only one. The same thing happens to my photos as well when trying to sync my ipod with vista; except my whole computer crashes each and every time. How do you format part of your hard drive in fat32?

  5. 5 Joe

    Hey, Josh. Pretty sure you can’t format your Vista drive for Fat 32 as it needs to be NTFS to operate, though you may be able to use a product like Partition Magic to create a new partition and then format it for Fat 32. Or if you have a USB drive format it for Fat 32 by right clicking on it and choose format and pick that type, then see if it correctly syncs pics that you’ve told iTunes keep in sync on the drive. Good luck, and let us know how you make out. Joe

  6.   6 Eric

    I have the opposite problem, photos I took with the iPhone are not syncing over to my computer. I thought syncing was two-way: anything new gets saved both ways. What is going on?

  7. 7 Joe

    Are you using Mac or PC, Eric? In either case, when you plug in the iPhone and there are new photos on it, you should be getting a prompt to import the pictures, with the option to keep the photos on it or delete them. The photos on Mac come into iPhoto, and on the PC it opened Adobe Essentials, on my test Vista system. Whatever the program, you should be getting that prompt, and it sounds like you are not.

  8.   8 Dustin James

    sounding like a broken record but…

    Running Vista Ultimate and having the same problem… I tried from a FAT32 external.. but the same dilio…

    I was afraid it was just me.. glad I googled it…

  9.   9 EricP

    I don’t know if this will help anyone, but, if you have Adobe Photoshop I have found out that if you save your photos as a “png24″ file (from file-save for web and devices-then select png24 instead of the usual gif or jpg). I know this is a crappy workaround, but it’ll do until the new update from Apple rolls around.

  10.   10 cherhall

    Thanks to the poster who suggesting synching photos from an external drive!!! Have been agonizing over this issue since I got my phone. I figured it had something to do with Vista, since I’ve had video/photo issues with iTunes ever since I switched to Vista. But synching from my portable hard drive did the trick!! Thanks again.

  11.   11 SuperMagnetMan

    I am syncing my iphone with macbook pro and I have the exact sme problem. The iphone created this mystery foler and puts certain photos in it and other photos in the Camera Roll folder. I have not been able to find any way to sync the Camera Roll photos. The other photos seem to sync OK but the camera roll is dead. It seems the only way to get it out of there is to email it to someone – which of course, is a crappy solution.

    Is this just a blunder from Apple that we can expect a quick fix to or did someone actually think that people wanted to take photos that went to a folder that they could not get to?

    Help appreciated

  12. 12 Joe

    When you plug in your iPhone, on which you’ve snapped new photos, iPhoto automatically launches to import the new photos into iPhoto. Though I hate iPhoto because you cannot organize by literal folders, only albums, I allow it to import, then I drag those pictures to real folders. Anyway, my point is you should be getting a prompt to import the photos into iPhoto. As for syncing other photos you want to keep on the iPhone in your iPhone photo library, in my case I sync to a literal folders, skipping the iPhoto thing all the way. But if only some of your photos are coming across and not others, that’s weird, as the only people who’ve reported the same have been on Windows machines, as far as I know. Hopefully others will chime in here with additional help. Joe

  13.   13 Neil

    I have the same problem with my Ipod 80G. Pictures will not sync. I get a similar message Ipod cannot read a .jpg file. This only occurs on my Vista operating system. Spent hours with Apple on the phone. They claim they never have heard of this issue and will not replace or refund the money I spent on the IPOD. They claim it still plays music. Some pictures approx .1% do sync, but they have horizontal lines through the picture.

  14.   14 Ken

    I just plugged in a little 5 gig FAT32 flash drive – drug over 1200 photos from my Vista system drive – applied and bam! All good. All the pictures moved but in my case it only kepy my primary folders and nuked my sub folders.

    I have used a lot of PDA’s to date. Since I collect a lot of contacts via a CRM – this and the 700P are the only PDA phones that can hold my contacts. This device has far more potiential and out of the box. Not only a cool PDA and IPOD, but so far a great phone, and by far the best integration with bluetooth that I have experienced.

    Thanks again,


  15. 15 Joe

    Glad to hear you got it working. I agree with you on the iPhone’s potential, and I’m looking forward to the upcoming updates to add more features, but as for Bluetooth support, I find it lacking. I can’t, for instance, click on a contact in my Mac’s Address Book program and send an SMS from the Mac via the phone, the way I can with my Nokia 6682. Nor can I Bluetooth notes between the Mac and iPhone the way I can with the Nokia, or sync notes the way I can with the Palm Treo 680. All the same, I don’t see switching back to either of those phones. I’ve read that the Notes feature in the upcoming Leopard OS X release will sync with iPhone notes – that will be great. Hopefully even more expected features, like voice dialing or the ability to redial the last call by tapping the iPhone Bluetooth Headset button will also appear, by way of updates. In the meantime, you’re right about the potential out of the box – now we need to see Apple open the box, so to speak, to make the iPhone the truly powerful, great device that it can be.

  16.   16 lola

    by god! I have finally found a website that had the same problem such as I! nm…

    But yeah, I was frustrated last night due to this. And thank god, I have finally found this place and I decided to give it a go and try out the “use photoshop and save it as png24″ file and lo and behold!!!!! It worked at last. yes! Thank you so much for creating this post and thank you for all the people who gave out solutions to the problems. I will now proceed to copy/paste this page and bookmark it. You guys are awesome! Thank you

  17.   17 Sin

    I was having the exact same problem with Vista until I bumped into this Blog. I added the pictures to an external USB back up and sync’d from there – NO PROBLEM! I’m still irritated that the problem exists but this work around fixed it.

  18.   18 CHiEF

    Ok, I was having problems getting photos from my iPhone to sync over to iPhoto…it seems the iPhone just wasn’t mounting in iPhoto at all. When I unplugged the phone, the image of a camera that said “Apple iPhone” would remain. I read on another site that you should just unmount that, then restart iPhoto, but that didn’t work for me. What ended up working was deleting all the photos in the trash (some 800 or so odd flicks that had accumulated over time because I hadn’t realized weren’t really deleted when I pressed delete in my photo library). After that, the iPhone was recognized by iPhoto again and the pictures I took were once again being imported.

    I suppose it could just be a coincidence, but I’m guessing it had something to do with importing working now.

  19.   19 Macman


    Just to let you know you’re not crazy… I was just having the same problem where iPhoto would not mount the iPhone. I found your comment, emptied my trash, and lo and behold, the iPhone suddenly launches iPhoto and imports my photos! I suppose it was some overflow from the iPhoto trash that was not allowing the phone to mount – pretty strange.

    Glad you posted this! Thank you!

  20.   20 Pam

    Same problem here!!! Oh I’m so upset. $500 I paid for this? I am no Computer wiz so I know nothing about FAT and 32?? I have a new HP PC running Windows Vista. I really HOPE Apple will come out with a fix for this. I have a lot of relatives scattered all over and had some nice pics on my PC to use as ID photos…this stinks. The phone is okay…but I have to say for $500 I could have got a car charger, a printed user manual, and a case!!! I also don’t think I can send picture messages (MMS) that I can tell.
    Sort of makes me have buyers remorse…I just extended my AT&T contract for two FREAKING years…for this!!! I hope they step up and start offering some customer service because I’m starting to wish I’d bought the Nokia N95 online…same price and I wouldn’t be locked into a contract.

  21.   21 Susan

    Having the same problem with Vista…How do you use Adobe Photoshop to save as a png24 file?

  22.   22 Vincent

    Windows Vista Home Premium: iTune only syncs photos from an external FAT storage device. It has to be a bug in iTune.

  23.   23 Julie

    Thanks for all the help here! Bought my iPhone yesterday and have been pulling my hair out trying to get photos over. Only a few were synching, and several of those were corrupted. Found this topic and put the photos on a thumb drive, they sync fine now. THANKS!!!

  24.   24 Boykin

    Huge Thanks to CHiEF. iPhoto on my MacBook was not launching when I plugged in iPhone so I had a bunch of photos on iPhone that I could not transfer to computer. Emptied trash on MacBook, plugged in iPhone, iPhoto launched right up and photos are now syncing. That was bothering the crap out of me.

  25.   25 Martin

    Just got my Ipod Classic and having the same problem! Running Vista Ultimate..Terrible!

  26.   26 Bil

    I too have the exact same problem. I’m using Vista Home Premium with iPhone. I would like to try one of these workarounds until / if it gets fixed in a future upgrade. What exactly is a 5 gig FAT32 flash drive? I’m hoping it’s something simple like those portable usb deals that’s the size of a thumb and sometimes used as a keychain? I might try the Photoshop way also. But if that flash drive is what I think it is, I’ll go for that. Thanks!!

  27.   27 David Townsend

    Do you have a RAID disk on Intel motherboard. Known issue and will corrupt raid array if using itunes photo sync. Solution is to download latest Intel Matris storage manager rom Intel web site.

  28.   28 Paul

    I’ve had the same problem with photos and had already accidentily discovered the external drive thing. But there was still one photo that didn’t sync – who knows!

  29.   29 Royer

    Vista ultimate also here and im transfering some pictures right now..and….it works..this is gonna take a while.. only 2 gig stick and like thousands of pictures.. ipod classic 160 gig

  30.   30 Joy

    I have tried transferring pictures from itunes to iphone. Then I transferred a wrong photo and trying to delete it while connected to my friend’s laptop but I can’t find the photo I transferred. I want to delete that photo. I’m hoping somebody can help me regarding this one.

  31.   31 Rodrigo

    Same problem. iTunes makes no sense. iPhone makes no sense. Why not treat iPhone as a pen drive? Why do users have to become experts in awfull things as syncing and filesystems? Come on Jobs, you are making customers hate a potentially wonderful device (I don’t dare to call it a cell phone) as iPhone.

  32.   32 Fred

    I was having the same problem (vista Premium) with errors syncing photos with my 80G 5G iPod. I tried the following and it solved the problem.

    0 – Quit iTunes

    1 – Go to “START > Search”.

    2 – Select “All files and folders”, and make sure that you are searching over your entire main hard drive.

    3 – Then, type “ipod photo cache” in the blank, and click “Search” to begin searching.

    4 – When the search is complete, delete any “iPod Photo Cache” folders that you may find on your computer, by pressing the Delete key, or dragging the folder to the Recycle Bin.

    I found this in the following thread.


    What might have helped was I’m moving my iPod to a new computer (also vista) and I selected only one folder of photos to sync. Still, I hope the above helps.

  33.   33 pocketaces21

    Thanks Fred. I have a new Windows Vista computer and had previously synced iphone with our old computer. I could not sync on the Vista computer until trying your suggestion. After deleting the ipod photo cache folder on my hard drive it worked fine. Thanks again.

  34.   34 Stuart

    FAT solution works perfectly. For folks who don’t know a file system from a nail file, the easiest answer is to copy your photos to a USB flash drive. It doesn’t have to be a big one, your photos are probably not that large. The only other trick is to be sure to delete the iPod Photo Cache if it was copied over to this USB flash drive. Point iTunes to this location using the Photo tab and then Apply and Sync.

  35.   35 Muaitai

    Hey Stuart, I got it right, for some reason iPhone and Ipod cannot ready from NTFS so the best way to circunvent it is to use a USB Pen Drive.

  36.   36 stradavarius

    I don’t even get a chance to sync b/c I am getting the same weird errors when trying to import my pictures from a memory card to the Vista PC. The picture will be split down the middle with one side shifted up or down, or half the picture will be grayed out. Copying and pasting the pics gets the same errors. Importing from the same drive using the same card reader works fine on an MCE2005 pc (NTFS formatted). I can’t find the same errors anywhere else.

  37.   37 anton

    i had the same problem synching to a mac os x running tiger. i saw on another blog that the problem was associated to synching through a USB hub, which is how i had it set up. i connected my iphone cradle directly to my mac and it not only work for all photos perfectly, but it was much faster.
    a bit of a pain to have to swap usb plugs, but at least all my photos upload correctly.

  38.   38 Daniel

    Thanks! I uploaded the pictures from my flash drive and it worked perfectly. I was having the same problem, and I have windows vista. Thanks!!!

  39.   39 tim

    sorry guys looks like its a prolem with vista combined with the ipod. i though it was just me though aprox. 1/2 of iphones or more & videos & 3gen nanos are doing this.
    best thing to do is transfer your photos to xp then try again.
    i know that many people use their ipod as a back up for their photos, i did and it saved my life?? (well no quite, when my computer crashed it was the best source for me to get them back)
    you can go in to my computer and click your ipod and copy your photos staight there. they won’t be visable on your ipod but they will be there. so they will be saved should your computer crash.
    for the moment though you’ll have to wait for apple to realease an update (hopefully soon)
    if you need help to back up your photos. say i’ll help.
    tim baker

  40.   40 Daniel

    This sucks.
    Can it possibly be that Apple didn’t discover such an obvious failure?
    I m begining to beleive Apple tries to make vista look bugy by putting vista relatetd bugs in their own software.

  41.   41 Andre

    Andre Says: Your comment is awaiting moderation.

    December 29th, 2007 at 7:02 pm
    hey guys when i am running vista i am able to sync perfectly but when i pulg in my iphone i don’t get a prompt to import the photos, the icon isn’t even there in my computer, any ideas, thank alot ppl

    sry bout that i meant i am running vista

  42.   42 tim

    best thing u can do is go the long way round-
    my coputer through start
    then click on ‘Andres iPhone’ or wht ever u called it, then go in to the source file for photos and copy and paste them there- this may not work though, but worth a shot- this will NOT work with music for copy pretection reasons,
    but i have one question for u- why get an iphone? the second gen may be good but 1st is to dull, and needs to mush doing to it.
    let me know wht happens- if any one else needs help email me at [email protected], no spam though cause i will just block ur ip address- which for security reasons i am tracking but not doing anything with unless u send me spam.
    thanks, and happy to help

  43.   43 Seamus

    This is my solution for users of Vista and itunes 7.5
    I also could not copy photos to ipod 80 G. Always looks like it was copying and folder appears in ipod directory when I double click it. However when I eject the ipod, there are no photos on it.This is how I have got around this. I use a usb mass storage device( i,m sure any picture card will do ). It is easy to copy pics to these. When ipod is connected double click it, then click photos then click sync. Open the drop down box and click choose folder. Scroll to computer and dbl click it and then scroll to whichever removable disk your pics are on. Click all pics and then sync on bottom right hand corner. This works for me every time.
    Hope this helps somebody until apple improve their software.

  44.   44 Roshan

    hi all, i have been using iphone for 2 months now, lately i copied pics from my i phone to iphoto and while doing so i saw this option at the bottom to delete pics from camera after copying so i checked it and now my camera wont work, it doesn’t save any pics i click its just blank boxes in the camera roll and when i try to view them it just returns to home and they are all gone unsaved on my iphone. please help me fix this prob….any one 🙁

  45.   45 Mike

    hi all – i thought i was going crazy. i’m running vista home premium. my photos would sync perfectly from some folders and not from others. it would only sync certain photos all the time – no matter how many i had in the folders. i would also delete the photo cache and delete the photos from the ipod between each retry. the only difference in my configuration that i know of is that the folders it works with are on an internal SATA harddrive. the folders it doesn’t work with are on an internal EIDE harddrive. i’m wondering if it specifically has to do with EIDE since others are experience iTumes sync working on external USB.

  46.   46 A.J.

    I had the same photo importihttps://joeygadget.com/files/2007/07/04/ng problems, syncing pictures from my iphone to my mac would error out after a few pictures. some of the pics would be in iphoto and the rest would error out. after i stopped using the usb port in the keyboard and used the usb port on the mac i no longer had the problem. try that…Good Luck


  47.   47 tim

    hi people
    erm, well i am using a hp laptop, with vista home premium, and i have 2 usb prots on it, and no diffrence, though if u r using a port spilter or something may b worth a shot.
    for the problem with no camera working the best bet is to go here :: https://selfsolve.apple.com/GetWarranty.do :: plug ur iphone in 2 ur computer then go to tht web page and follow the instructions, this will help locate the problem, and if there is a problem with the driver- which is probably is- then this should help solve it, let me know how it goes. email me if u have more problems or post here [email protected]

  48.   48 tim

    Hello yet again
    i have now had a serious problem with my ipod, basicly it froze so i did the normal- reset it, bu then it restarted over and over, so i had to take it back to the shop- i tried to pluging the computer, but the store said ‘its got to go away for 2 to 4 weeks’ 🙁 so im left ipod less. though if after 4 weeks it doesn’t come back im going in to demand a new one. However should this happen to anyone else, or to me again is there any easier way to solve it?

  49.   49 LML4400

    Having a similar problem but with Windows XP and my iphone.
    I even tried emailing the photo to myself, viewing it on the phone only to find that there is no way to save the jpg in the photo file on the phone.

  50.   50 LML4400

    I have been able to get photos from the phone to the PC but not the reverse

  51.   51 drumchapelloyal

    I recently had to restore factory settings on my PC (windows xp) but before I did I transfered all my family photos to my iphone (different sub folders) but when I try to store them on the computer the photos can’t be located.

  52.   52 Rocky

    Fred was 100% correct. Delete the folders called ipod cache and take a pic and re-sync to computer.. Thanks

  53.   53 Frank

    I can sync photos to my Iphone. The problem is I can’t add additional pics to this phone without the original pics being replaced. It seems I can only have one folder of pics on the phone. Is there a way around this so I can get more pics on the phone. Iphone 2G running 2.1

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