The issue you’re describing sounds a lot like it might be a potential IP address issue, exposed when Sonos reboots their system every time they update their software. Try this:

Unplug all your Sonos devices from power. While they are powered off, reboot your router. Give the router a couple of minutes to come back up, then plug in your Sonos devices.

A more permanent version of this is to go into your routers software and assign reserved IP addresses for all your Sonos…if that is possible (it isn’t always a feature you can access, check your router’s manual). 

Note that this has nothing to do with signal strength of your network, it is merely an addressing issue, making sure the packets of data are being sent consistently to the correct device. 

Thanks Bruce. I’ll try this...but it doesnt explain why the same tracks each time play a few beats and then skip.  The same tracks on different playlists - same audio source - play fine.  Its a mystery introduced with the update a couple of months back. 

Well, there is also the potential for wifi interference , where the speaker is being affected only when the stream reaches a certain density in the stream. But you said the network was ‘strong and fast’, but I’m not sure how that is easily measured, since the ‘network’ we are talking about is the WiFi or LAN between the Sonos devices and your router, and/or the speed between your router and your NAS. 

Additionally, I’ve not had any issues in my 20+ speaker system, which I play from my WD NAS, so it is unlikely to be endemic in the Sonos software. And you indicated that it started with a software update, traditionally where Sonos requests new IP addresses for their connection to the router, and if the router has gotten in a ‘bad’ state, it can offer up duplicate IP addresses, which the suggested process would, at least temporarily, fix.

However, if you feel that the few minutes it would take to test my theory are too much, I’d recommend that you submit a system diagnostic within 10 minutes of experiencing this problem, and call Sonos Support to discuss it.

There may be information included in the diagnostic that will help Sonos pinpoint the issue and help you find a solution.

When you speak directly to the Support staff, they have tools at their disposal that will allow them to give you advice specific to your network and Sonos system.

This is definitely a problem and not an IP or connection problem. I have 2 systems in 2 houses and the system skips the same songs in both residences. This is a software problem of some sort. The songs are owned by me, so there should be not licensing issue. I need to do some more diagnostics, but this is definitely a playlist issue. Not sure if I skip to the actual song if it will play...need to check. But either way, this renders SONOS almost worthless if it cannot play a playlist as constructed.  I am not even able to force it to play, it just keeps skipping. 

It has gotten worse after the most recent software update. 

Sorry for the typo’s 

Look for the three dots in the lower right of your post, they give some limited ability to edit.

You are only able to edit for a short time, then the edit feature is removed. But thanks for your insightful response to the initial topic.