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.
http://www.kozco.com/tech/clips/millerGuitar2.aiff
Koz
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 http://en.wikipedia.org/wiki/Audio_Interchange_File_Format ). 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 ( http://manual.audacityteam.org/o/man/faq_installation_and_plug_ins.html#macff ). 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 http://wiki.audacityteam.org/wiki/Release_Notes_2.0.3#Large_Projects .
Gale
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,
G
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.
Gale
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 https://forum.audacityteam.org/t/ipod-classic-aiff-format-metadata-recipe-for-problems/30376/6
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?
Gale
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.
Gale
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. 
Is this with the cable still connected to the iPod, or with the cable disconnected, so that the iPod is on battery?
Gale
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. 
Let me amplify
Turn that dial all the way up to 11.
In the first test,
I open with Audacity,
It recognizes a file with some issues
but it handles those issues so I can work with it in Audacity.
However, when I write out a copy
it does not write out a fixed aiff file.
In the second test,
I open with Amadeus,
Behaves like Audacity.
However, it writes out a corrected aiff file.
I just rechecked to see
and yes the Amadeus files work correctly in iPod.
One other wrinkle.
Peak finds fault with the Audacity resaved copies of the split files
Peak has no issue with the Amadeus resaved copies.
It would be most helpful if you avoided writing in abbreviations.
“just a letter”: What does that mean in English?
“and a number”: Likewise, what does that mean?
“no title, no artist”: If you are referring to metadata, please say so.
“no work”: We’ve had this phrase before, but I’m still not clear about the details. Assuming that you mean the same “no work” as in this post, you go on to say “iTunes looks at it, gets an error and says I will fix that for you.” I doubt that iTunes actually said that. What was the actual error /warning from iTunes?
Precisely what issues?
Not until there is a clear description of the fault.
In what way do AIFF files produced by Audacity fail to meet the AIFF file format specification? If the files do not meet the file format specification, then that is a bug that can be addressed by the Audacity developers. If the files do meet the AIFF file format specification, then it is not an Audacity bug.
Does this file play correctly on your ipod? http://www.kozco.com/tech/clips/millerGuitar2.aiff
This is the problem.
Can you multi export an Audacity project as ascii files
and get them to play correctly on an ipod.
I have not been able to
and have tried several ways.
I can multi export an Audacity project as WAV files
and it works perfectly.
What can I clarify?
I presume that you mean “AIFF files” and not “ascii files” ?
We are trying to work with what you tell us, but unless you can tell us clearly then there is little anyone can do to help.
As a start, you could tell us if this file plays correctly on your ipod: http://www.kozco.com/tech/clips/millerGuitar2.aiff
The link opens and plays in safari.
Not sure how to download to my computer.
Cannot see source “View Source” is grayed out.
Did you run a test on Audacity 2.x like my issue?
Did you split a project as aiff and load to an ipod?
I would be glad to split your file if I could get hold of it.
As far as I can see so far in this very hard to follow topic:
- Exporting multiple WAV files with no metadata play in iPod
- Exporting multiple AIFF files with or without metadata do not play in iPod
- Toog could play Koz’s single “guitar” AIFF file (that has no metadata) in iPod - we do not know yet if audio_pete can do so.
- Toog could not play AIFF files created by export selection on iPod.
@Koz - did you make this “guitar” AIFF file from a complete track (FIle > Export), or File > Export Selection?
Gale