Yes, we've experienced the same thing. Haven't noticed skipping tracks, but we normally play music in the background via Pandora (paid subscription, so no ads.) If it skips, we wouldn't really notice. But we do notice it just stops playing randomly. 

It's especially noticeable at night because we use a single white noise track from an album from Spotify (also paid subscription). We set it to repeat 1 and enable crossfade, so the white noise is constant for sleeping. Well, when it just randomly stops playing in the middle of the night, that defeats the purpose and often actually wakes us up. 

It seems like it all started for us about 3 or so weeks ago. Our whole system (all speakes) needed an update to keep using them. I think that's when our problems started.  

Just last night and this morning is the the worst it's been. We were randomly able to restart it the multiple times we awakened, but usually with lots of effort closing/reopening the app, clearing cache, etc. Both iOS and Android apps. I'm not convinced our messing with the app even helped, and may have just been timing. 

We're seeing errors in the app that others have reported:

"No connected products" (but then going to settings, all of our speakers are there.)

"Something went wrong" (when trying to start playing music) 

"Couldn't play content. Try again."

I think tomorrow night we'll just use a $30 bluetooth speaker from Amazon. We use that on trips away from home and it actually works consistently. Highly recommend the Oontz Angle for super cheap, "meh" level of sound quality, but 100% better sound than our thousands of dollars worth Sonos system that won't pay anything! Or wakes us up by abruptly stopping. 

It sounds like there may be some network interference to me. 
Have you tried powering off everything: router/network, speakers and your phone. 
Wait 5 minutes, then starting with the router/network, power it on and allow it to fully boot.

Next, power on each speaker, allowing it to fully boot before you power on the next. 
Then power up your phone and connect to your system.

I have tried rebooting several times. Will try again reconnecting as suggested. We’ve never had this problem before and nothing has changed so it’s really strange.

It’s not clear what order you’ve rebooted in, but pay particular attention to the order that ​@Pools-3015 mentions, as it is important to clear some parts of what can be considered ‘simple’ wifi interference .

Things change all the time, behind the scenes, from the router’s software, to neighbor’s WiFi, to even solar activity, much less potential items in your home beginning to fail. Don’t ignore things that you don’t know about in this process, and don’t assume that ‘nothing has changed’.

I rebooted in exactly the same order and it’s still not working. I’m on the verge of selling my speakers it’s made them almost unusable, it’s the most frustrating experience.

Then I would recommend that you submit a system diagnostic within 10 minutes of experiencing this problem, and call Sonos Support to discuss it. Don’t post the resulting diagnostic number here, they get sensitive about GDPR.

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.

I have the same problem….I have tried all the solutions and stiil get  “try again later”…..”timed out” ….”something went wrong” message consistently for the last three days...but has happened at least weekly for months...my wi-fi has no problem with TV, internet, and streaming from bluetooth of other streaming services...I’m pretty fed up…

Moderator Note: Modified in accordance with the Community Code of Conduct

This issue has led to finding a competing product to replace all Sonos in my life. The software running on these devices has deteriorated to an unacceptably low quality. Network connectivity becoming an issue being blamed on everyone else’s networks proves their support has also tanked. I’m considering adding a caveat to any future job postings to discourage engineers with Sonos on their resume from applying. Quality software engineering starts with accountability and Sonos has declared it is not a priority. Before any half-wit tries flexing their brain cell, I have gone so far as to create a dedicated 2.4 ghz network solely for my Sonos products only to find the same problems. Bye Sonos, what a sad and pathetic fall from the mountain top. How’s your pride though?

...I feel your pain….However, FYI...I am enjoying a 3 week stretch of “uninterrupted” connection without any failed service messages. My solution?...once connected?…maintain all speakers in an “on” state 24/7...control only volume. Rather than switching speakers on of off, use only the volume control. Rather than turn off any component, reduce volume to “0” to maintain the network connection.

Not sure I understand your solution, since there is no way to turn off most Sonos speakers other than unplugging them from power. Only the battery powered / portable speakers have on/off buttons. 

Using pause on a stream is the same as turning them down to zero, other than it stops the consumption of the stream. If you’re listening to a playlist, that should mean you wouldn’t lose your place. 

When rebooting be sure if leave device unplugged for at least a minute.  If there are major problems problems, unplug everything (all speakers, router both power and internet connection, and any splitters)  I use to do a lot of PC and router setup and learned that a lot of settings are not immediately released from cache. 

Same thing for me. Everything has been working just fine and suddenly it all goes to s***, with nothing (knowingly) having changed with our wifi and other network settings. We are long-term Sonos people and have nearly 20 of their speakers and Amps.  It’s wonderful when it works….until it doesn’t and then it’s a nightmare to troubleshoot….

Unfortunately, much of your network can change without interference from you, from updates done automatically to your devices, including your router, to outside influences, such as a neighbor setting up a new WiFi system. It would certainly be nice if networks were a closed system, but unfortunately, that isn’t the way they work. 

I have over 20 of Sonos devices, and an unsupported 5G modem/router/network, and I don’t have any issues, currently. I have, in the past, struggled with a microwave going bad, and bleeding WiFi disturbances, as well as new neighbors, who set up a newly placed WiFi router which interfered with my own signal. 

Sonos, being a networked device, turns out to be as good as the network it is tied to. Given the challenges of networking, some care needs to be taken, it has never been a ‘set and forget’ system.