The same thing is happening to me.

The music I downloaded is FLAC from HD Tracks so it's a a very high bitrate.

I auto converted to both WAV and MV4A and while able to play on iTunes only skips through the album on the iPod without playing anything.

Looking at the file details the bit rate after auto convert was reduced to under 600kb

I was able to get the highest quality MP3 to play on the iPod but only after doing a hard reset on the iPod Classic after the sync.

Other music I ripped from CD and saved as WAV play fine.

Mike
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Well, I don't have an iPod classic, but I can convert flac to m4a during sync for my iPhone and it works fine. You're sure you tried m4a format, not AAC?

I tried that and it won't play on my iPod if I sync with MM.. they play fine when I sync with iTunes.

Just convert to m4a format instead, they work fine on iPod.

Important update:

So I decided to see if it's the encoding format or the sync process that's not working. I used the send to -> convert option using 100% VBR and used iTunes to sync it to my iPod... the play fine.

So it must be something going wrong with the sync process.

So I've had some issues getting my iPod Classic 80 GB to play tracks I've synced onto it with MM. Due to a request on my other help topic, I upgraded to debug version 4.1.0.1619 in hopes that it would work better. It hasn't.

My music library is made up of mostly FLAC files, AAC files purchased from iTunes, and MP3 taking a backseat with only a couple hundred tracks in that format. Most tracks I want to put on my iPod are FLAC. I have configured MM to auto-convert all FLAC files that I Want to put on my iPod to convert to AAC VBR 100% because I'm not going to use an out-dated media format (aka MP3). Yes, I know I could make life simple if I just chose V0 MP3, but I don't wish to. I paid $10 extra for the MM Codec Pack so I could use AAC so I'm determined :E

So the conversion/sync process happens without error. I check my iPod and all my tracks are there. Except I start playing one and it just starts going from song to song extremely fast without playing any of them. This tells me that the format MM is using is not iPod compatible. Also, I can play the songs fine on my iPod using MM.

I know I could submit a bug on this, but after my 10 years in technical support, I know most things are user error and very few things are actual software bugs. Due to this, I am open for someone pointing out something I"m doing completely wrong.

[url=http://i.imgur.com/NUZK6Nw.png]MM Settings screen shot[/url]

[quote]OS Name Microsoft Windows 7 Home Premium
Version 6.1.7601 Service Pack 1 Build 7601
System Manufacturer BIOSTAR Group
System Model TA890GXB HD
System Type x64-based PC
Processor AMD Phenom(tm) II X6 1055T Processor, 2800 Mhz, 6 Core(s), 6 Logical Processor(s)
Installed Physical Memory (RAM) 12.0 GB[/quote]