Apparently, there is a bug going around on third-party Google Assistant speakers that is breaking Routines on those speakers. Routines are still working perfectly fine on the Google Home, Home Max and Home Mini, but as for third-party speakers like the Insignia Smart Speaker, or the Sony LF-S50G, they aren't working at all. And it doesn't seem to be acting the same, for everyone. Some will get the chime at the beginning of the routine, but Google Assistant will only do one task. Others will get the "I don't know how to help with that yet" message, or the "Good Morning" routine will work but others like the "Good Night" routine won't.
Google has not yet commented on the thread on its support forums, so it's unclear whether they are working on a fix or not. But it would be very surprising if Google was not working on a fix for this issue. Especially since it is effecting all third-party speakers and not just a handful of users. It's a really strange issue for Google Assistant, and it only seems to have started in the past two weeks. So perhaps there was an update that was pushed out (perhaps on the server side of things) that broke routines for third-party speakers.
Routines hasn't actually been out all that long actually, so it's kind of surprising to see this type of issue come up. Routines allows users to create a routine of different commands it might give Google Assistant at a particular time of day. For example, for a "Good Morning" routine, you could set Google Assistant to tell you about the weather for the day, what's on your calendar that day, give you the latest traffic conditions and finish up with the latest news, while you are drinking your coffee. Routines are very customizable, and you can create your own, although Google does have a few ready-made routines that you can enable.