AIFF files will not play on iPod, will on iTunes

I’m using Audacity from the .dmg on a Mac Pro hex core with 24 GB RAM. Audacity is installed on a SSD boot drive and the data is stored on a RAID 0 combination of conventional HD’s. Using OS X 10.6.8.

I record streaming radio, my saved projects (.aup) are anywhere from seven to twelve hours long, sometimes I will save them in halves. The files are ~7-17 GB. I export selections from the projects in AIFF that are ~80 minutes long. The stream is mp3, 128 Kbps. I record on a Windows PC running Windows Seven, using Real Player, for logistical reasons. Then drag them to the Mac over the network. That way I can record on the PC while I edit on the Mac, and also do not have to relay on that stinking, crash-prone, Adobe shock wave flash player. Adobe, are you listening!?

I’m just an audio lay person, although I am a rocket scientist,…really. I export in AIFF so as to have a file I can edit without loss of quality before I export a final section for listening, which I want to be as good as possible. I understand that I’m not starting with the gold standard of recording, nevertheless… I drag the files into iTunes, where they play just fine. I import them into my iPod, and while it’s plugged into the computer it plays the files. However, once the iPod is disconnected, the AIFF files will not play on the iPod.

If I export from Audacity in WAV or AAC, no problems. Same with if I convert the AIFF files to either of those two while in iTunes. I called Apple tech support and was escalated twice, ultimately, to a senior tech spec., who didn’t have an answer, but would like to know what I find out. AIFF should be compatible with the iPod. In fact, some of the earlier AIFF files I created in Audacity will play on the iPod, but after trying to play, several times, those which will not, the early files will no longer play either. But, if I reset the iPod they will play again. Restoring does not help, except doing so will provide the same fix for the early AIFF files as a reset.

I realize I can work around the issue by not using AIFF, however, inquiring minds want to know…

Any thoughts?

Thanks guys,


All AIFF files will fail to play on a stand-alone iPod? Short, long, it doesn’t make any difference?

If you prepare your work in WAV, open it in iTunes and use iTunes to convert to AIFF, do those play? I think you can use QuickTime Pro to convert as well if you have that. I’m wondering if it makes a difference who makes the AIFF file.

Open the AIFF in QuickTime and Command-I invoke the INFO panel. What does that say?


All AIFF files will fail to play on a stand-alone iPod? Short, long, it doesn’t make any difference?

No, I exported one song, ~38 MB, in AIFF from Audacity, which would not play in the iPod. The larger file I am using (from which the prior song was culled) is ~850 MB.

If you prepare your work in WAV, open it in iTunes and use iTunes to convert to AIFF, do those play?

Yes, converting a WAV exported file to AIFF in iTunes results in a file that plays on the iPod, both the small and large files. In fact, if I convert an AIFF file in iTunes to AIFF, that will play also. In the get info section, iTunes, the extensions of the converted files change from AIFF to AIF. However, just going into the iTunes folder on the HD and changing the extension to one F does not alter its playability. In some cases, on an Apple PC, extensions can get a little funky, so it was worth a try.

I’m wondering if it makes a difference who makes the AIFF file.

Does not seem so. I converted both the small and long files from WAV to AIFF, and AIFF to AIFF, using WavePad, and they all played in iTunes and on the iPod.

Open the AIFF in QuickTime and Command-I invoke the INFO panel. What does that say?

In all cases the Quicktime format was : Linear PCM, 16 bit big-endian signed integer, 2 channels, 44100 Hz. That includes conversions in WavePad and iTunes.


— I’m wondering if it makes a difference who makes the AIFF file.—
Does not seem so.

Yes, it does. Only AIFF files from Audacity fail, right?

Correct. I answered in the context that we already knew that Audacity AIFF would not play and, so, were there anyone else’s AIFF files that would not play.

So far, only AIFF files created by exporting selection, in Audacity, will not play.

Am I the only one to whom this has happened?


Now you have to wait until one of us has time to stop what we’re doing, drag out the iPod, connect it, etc. etc. etc.


I made a nice AIFF file in Audacity 2.0.3 and it plays perfectly on both an iPod Touch and an older mechanical, spinning hard drive iPod.

This is the file I made.


If the iPod is on battery when unplugged from the computer, that is probably the problem - it will struggle with the extra calculations for any format that is unexpected in any way, or a file that has an unusual bit rate/depth or sample rate.

I was about to suggest the AIFF was unexpected compared to Audacity’s because I thought AIFF’s written by Apple applications are actually little-endian and have been for some years even on PPC machines ( see ). However an AIFF converted in iTunes does appear to be big-endian according to QuickTime Player just like an Audacity-exported AIFF. I only see one character difference in the header between an iTunes AIFF and Audacity AIFF.

If you wanted to satisfy curiosity you could install FFmpeg ( ). When you export from Audacity, choose “Custom FFmpeg Export” and click “Options…”. Choose “aiff” in the formats list and “pcm_s16le” in the codecs list. Click OK, add “.aiff” (without quotes) to the end of the file name, then export. This will give you a 16-bit little-endian AIFF instead of the normal big-endian.

What other differences could there be between an Audacity-created file and an iTunes created file? Does your Audacity-exported AIFF file have metadata? Does the order of the metadata change after conversion to AIFF in iTunes? You can check in a hex editor.

Please be careful. 13.5 hours is the maximum amount of audio that you can save in a 44100 Hz project, and less than that at higher sample rates. See .


Thanks guys for the response.

The guitar section played.

I save my long projects in sections.

Like everyone, I only have so much time. I’ll get to the other suggestions in the next couple of days.

Thanks again,


In the iPod without the cable connected?

Koz’s guitar track has no metadata (Artist, Genre and so on). Perhaps your files have metadata.

Any AIFF saved by iTunes will have Normalisation (NORM) and Gapless (PGAP) information added to the file.

If Audacity exports an iTunes-created AIFF file containing NORM and PGAP data, it duplicates the Normalisation information towards the top of the file (but removing the “NORM” designation from both instances) and removes the Gapless (PGAP) information entirely. This could be quite sufficient to upset iPod running on battery.


I have a similar issue.
Seems like the metadata is at the heart of it.
Aiff with metadata, not in track order and does not play properly.
WAV without metadata works fine.
Aiff works with iTunes and on iPad .

Am pretty sure I have/had an Amedeus aiff on my iPod worked fine
but,again no metadata. So maybe not apples to apples.

As I asked in your other topic

That is, if you save a single AIFF created in Audacity in Amadeus and Peak, do they empty the metadata? But they don’t do that with AIFF’s created by iTunes?

Have you tried iPod connected to the computer, to rule out battery power as the reason it will not play Audacity-created AIFF’s that contain metadata?

Please generate a tone or record something in Audacity then give us steps 1, 2, 3 to reproduce this
problem. Don’t use AIFF files already created by iTunes because we know Audacity modifies iTunes NORM and PGAP.

Tell us exactly how you are splitting the tracks using Export Multiple and exactly what you are typing into Metadata Editor. Tell us exactly in what way the exported files are “not in track order”.

Better still, please upload some AIFF files produced by Audacity Export Multiple from a tone or a recording to a web server so that someone who has iPod on Mac can try them.

Are you talking about AIFF files written by iTunes, including those converted by iTunes from WAV or AIFF files produced by Audacity?

If so, isn’t that a useful workaround to the problem?


cassette tape to mac os x 10.5.9
nearly always record side 2 first, so have to cut and paste to get sides in order
normalize to max minus 1 down click (12.0 to 11.7)
use point labels
multi export with point labels
export aiff 16 bit 44100

add to itunes library
itunes can play but songs out of order (see attachment)
ipad can play over icloud out of order

ipod classic does not play or plays first and then skips around without playing.

Not all code handles problems the same
I think Peak which finds the 2nd file on as bad no end of file
and ipod software have limited ability to handle a file that is not 100.00%.

comments on tiff
top album file splits reopened and resaved with Audacity, out of order but play in itunes
second album (unknown) file splits opened with Amadeus and saved, in order, plays in itunes, metadata gone
third album file splits from Audacity out of order, plays in itunes, skips in ipod, modified metadata in itunes added track number to name to see if helped
fourth album file split into WAV files, in order, plays in itunes, plays in ipod,no metadata
itunes.tiff (119 KB)

Thanks for testing.

Did you add metadata to these files? If so, exactly what metadata? Was it the same metadata for each track, apart from the track title and track number?

Do you mean you re-exported from a saved Audacity project?

As explained, I think the best test is to record something then export multiple and add metadata, not reuse files saved from iTunes.

So did it help with a) ordering the files correctly b) playing in iPod?

Could you possibly test with export multiple AIFF files with no metadata, if you have not already? Just name the files in each Audacity label and see the order in iTunes and if they play in iPod.

And please could you test the files playing on iPod when it is connected to the computer even if you normally would not have the iPod connected. If it is relevant it could help other users.


Time for an entry in Bugzilla.

First, none of these files come back out of iTunes .
I opened the Audacity file from the split in Audacity as an aiff file,
Then I saved a copy of the file as aiff.
No help.
I opened the Audacity file from the split in Amadeus as an aiff file,
Then I saved a copy of the file as aiff.
Lost metadata, but in order and played.

First the good news.
The files seem to play everywhere else just fine:
iTunes on my computer
iPad from iCloud ( maybe an apple copy, but one tape working on would have no copy)
Apple tv from iCloud .
The exports as WAV files work on iPod.

Now the word from Peak LE
I opened the Audacity file from the split with Peak,
The first file opens and a copy is saved.
None of the other files open
can’t find end of file.

Now the BAD news
Multi export song name, artist put in metadata editor no work
Multi export with song name as label, all same artist no work
Multi export with default letter for song name no work

I am not the only one reporting issues.

Please make a Bugzilla entry or give me access.

What does “no work” mean?
The Metadata Editor does not have a “Song Name” field. Do you mean “Track Title”?

The files when synced to my iPod
do not play.
It might play first song but then it displays the title to the 4th,6th, 2nd and back to the first
without playing a note.

The file is not right.
iTunes looks at it, gets an error and says I will fix that for you.
Amadeus does the same.
Peak says whoa wait a second, let me tell this guy the file has a problem.
iPod software does not catch error, has no code to handle the situation
and flies off in search of the end of the file.

Try to get the album to play a couple of times
and you have to restart the iPod
to get it to work with any song?
It’s so confused.

You kindly offered to test AIFF’s with no metadata. Are these tests with no metadata? If so, what does “no help” mean? Were the files out of order in iTunes? Did the files refuse to play in iPod when running on battery?

I think you have already said that if metadata is added in Audacity the songs may be out of order in iTunes. I’ll see if I can reproduce the “out of order” problem in iTunes, but if not, your steps above are not accurate enough for a bug report. :wink:

Is this with the cable still connected to the iPod, or with the cable disconnected, so that the iPod is on battery?


The last “multi export…” is no the metadata test, just a letter and a number no title, no artist, no work.

Exact same test with WAV is a success.

“out of order” is less important than the fact they do not play.

I will run a test with the iPod plugged into a power socket but not connected to the computer.

Plugged iPod into wall socket
Tommy by the Who, all titles,in order
Ran through tracks 1 to 23 without playing a note

Crusin’ with the classics
Ran through p1 through p10 in about half a second

Size is not an issue, I had I side of a bluegrass tape on my iPod before in aiff.
Took it off to replace with full copy split into songs
but then that did not work. :astonished: