Are they on wifi or Bluetooth?
If on wifi, are you trying to group them, to play the same source? If so, get the source playing on one, and then add the other to the group. 
Or, please explain more clearly what you want to do. 

I hate to ask, but can you post what your network consists of? It may be a simple configuration change that you need to get things working as it should.

It’s  giving the same problem on both sides Wi-Fi and Bluetooth.  I am trying to get both speakers to play from the same source. There doesn’t seem to be any rhyme or reason to when the issue occurs either.  These are Sonos roams. If that makes any difference.  

I’m sorry,  I don’t understand the question.  If it’s a configuration issue, I am all ears

Are you saying that sometimes it works?

Have you tried it in the sequence I said in my first reply?

Just as a precaution, make sure your system (app and speakers) are all up-to-date. 

This was actually the first thing that I did

What source are you playing from? Does it allow play to multiple speakers?

How many speakers can i connect to my ERA 100 2 room

Depends on what you mean by “connect”.  You can group as many as 32 speakers together.  But that is temporary.  For a permanent room, you can have a stereo pair or a soundbar/Amp + surrounds, with or without subwoofer(s).

Looking for a whole house system if I get the ERA 100 how many speakers can I connect to that and scatter through out the house?

You can have 32 Sonos devices total on a system, plus 32 controllers active at the same time. 

ok, so we are clear before i place my order, if i get the ERA 100 2 room, what device (speaker??) do i purchase to extend this to a whole house type set up?  Do i purchase and additional era 100 or is there just a speaker that i can purchase instead of another era 100?

Any Sonos device currently sold can be used in the same multi-room environment.  They all will allow grouping of individual rooms.

So if I purchased the ERA 100 2 room What device do I purchase to make it so I have speakers throughout the house connecting to my ERA 100

As said any other Sonos speaker will Group with your Era-100. 

You just need to purchase the number of Sonos you want and add them to the Era-100’s setup.

You do not need anything else.

Do you have a specific Sonos that would work the best to pair with my ERA 100 to accomplish my whole house effect?  If you were buying this system new, what Sonos would you buy to pair up with my ERA 100 2 room system?

I don’t know how to say it any clearer:  ANY* Sonos device you can purchase will be able to be grouped with any other Sonos device for whole-house audio.  You can group and ungroup to your heart’s content.  Read about it here:

https://support.sonos.com/en-us/article/group-and-ungroup-rooms

You can group them (pairing is something different) with a single Move, all the way up to the Ultimate Arc Immersive Set.

*Note:  Ace headphones can only be connected to a Sonos soundbar for TV sources.

I don’t know how to make this any clearer, I am asking you for advice on your product.  Sorry for not using the correct terminology but I am sure you understand my question.  Do I need to buy multiple ERA 100’s or will the ERA 100-2 room and just buy a speaker only to GROUP.  Your link does not specifically answer my question.

Not sure why you can’t answer my question.  If you owned an ERA 100-2 room what speaker would YOU buy to group, to accomplish a whole house system.  

Anything listed here (Except for the Ace headphones): https://www.sonos.com/en-us/shop

In other words, there are no special requirements to accomplish whole house audio.  Just buy whatever Sonos unit you wish to buy and they will all work together to give whole house audio.  That’s all you need to know. 

PS - All the posters in this thread are users like yourself.  Sonos employees are marked as such.  We are simply users and it is not our product.  Just an FYI.

If i was buying new,

TV Room Arc Ultra, Sub 4, two Era-300

Bedroom Beam, mini-Sub, two Era-100 if it has a TV two Era-300 if not

Kitchen two Era-100

Office two Era-300 either mini-Sub or Sub 4 depending on room size

Bath Era-100, maybe two

Dining room Era-100s two or four depending on room size