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Looking at your pictures, I recommend that you put both the relay and the chime connector where the transformer is located; you don't really have enough room where the chime is located to install them and be able to put them out of site. However, since your transformer is on the 1st floor and your chime is on the 2nd floor you will need to run additional wires between the 1st and 2nd floor to be able to make the connections shown in the diagram.
What is the voltage rating of the low side of your transformer? 16V? Do you know how much current you are getting at the coil side of the relay? One other question, do you know which version of the Chime Connector you are using? SS came out with a Beta version that was supposed to fix the digital chime issue (it didn't seem to work) and if you recently got the Chime Connector they could have sent you the Beta. I haven't tested this configuration against the Beta version.
I tried to trace out your wires from the picture but can't see all the runs and connections clearly. I can only see one wire attached to the left transformer terminal that runs to the chime connector that correlates to the dark brown wire in my diagram. Is there a second wire on that terminal that goes to the Transformer connection on the chime (the brown wire in my diagram)? I can't read the label in the picture so I'm somewhat guessing at what each terminal is. It sounds like you are getting power to the relay since it switches but the power isn't getting sent to the chime. It also sounds like your voltage is getting cut in half. Try removing the diode on the switch side of the relay.
It sounds like the doorbell connections aren't staying closed long enough to allow enough current to pass through to close the relay and trigger the chime. Do you have a 1A diode across the two doorbell terminals (most doorbell diodes are 1A, 50V)? If not, give that a try. The downside is that installing this diode could allow enough current to continuously flow that the chime chimes constantly. It definitely sounds like the issue is at the doorbell, not the rest of the setup.
Hi ScottS525 - Yes, I'm still available to help if needed. I'm not sure if Birdie00 ever got this working. I could never figure out why it wasn't working and probably would have needed to get my hands on their build to see what was going on, but that isn't really practical in this forum. BTW - SimpliSafe is now beta testing a new chime connector that is supposed to enable you to use their doorbell with a digital chime. I'm not sure when or if this new connector will be available.
Hmmm...the relay should have a clear housing where you can see the coil and the switches, you should see the switches close when you press the SS doorbell. If the switches are closing then the next thing I would try is to replace the diode on the switch side of the relay. It that still doesn't solve the problem them you should check to make sure that all of the wires that are added in my diagram, the ones that don't get used when you just hook up your old doorbell, are good. The best way to do this is to run a continuity check with a multimeter. If all those wires are good then I'm somewhat at a loss to why it isn't working, it just seems like a connection isn't being made somewhere.
Sorry for the delay in getting back to you, I've been away on vacation. Since the relay is lighting up when you press the SS button it seems to be getting power so the problem is probably between the transformer and the chime, or the relay and the chime. Did you check to make sure you had the wire from the transformer to the chime connected to the transformer terminal on the chime? If so, I would do a continuity test on that wire to make sure it isn't broken. If that checks out then I'd do a continuity test on the wire from the relay to the chime. If that checks out then the only other thing I can think of is to double check that the diode on the switch side of the relay isn't installed backwards. I hope that gives you a couple of areas to check.
Isn't that the wire that connects to your front doorbell? The one that is connected to the transformer terminals on your board should be connected to the low voltage terminals on the transformer and just transfer the power from the terminals on the transformer to the terminals on the board so you don't have to run other wires back to the transformer. If the other wire isn't for your front door then maybe it connects to a back doorbell.
The red light on the relay comes on when the switch is closed and the chime rings so it makes sense that it went off when the chime stopped. Looking at your second picture it looks like you have too many connections on some of the terminals. There should only be one wire connected to the "Front" terminal but you have two. The red wire running from the relay to the "Front" terminal is correct. The white wire running from the left transformer terminal to the "Front" terminal is incorrect and needs to be removed. Where is the wire that has the sheathing around it that has both a red and white wire inside of it, with the white wire connected to the left transformer terminal and the red wire connected to the right transformer terminal, coming from? My guess …
The red light on the relay comes on when the switch is closed and the chime rings so it makes sense that it went off when the chime stopped. Looking at your second picture it looks like you have too many connections on some of the terminals. There should only be one wire connected to the "Front" terminal but you have two. The red wire running from the relay to the "Front" terminal is correct. The white wire running from the left transformer terminal to the "Front" terminal is incorrect and needs to be removed. Where is the wire that has the sheathing around it that has both a red and white wire inside of it, with the white wire connected to the left transformer terminal and the red wire connected to the right transformer terminal, coming from? My guess it that wire is connected to the low voltage terminals on the transformer and just provide low voltage power to the transformer terminals on the circuit board which you are then using as connection points rather than connecting directly to the low voltage terminals on the transformer. If that is the case then that should be OK as long as you don't have any other wires connected directly to the transformer low voltage terminals. Try removing the white wire I mentioned that currently runs between the left transformer terminal and the "Front" terminal. If that doesn't work try replacing the diodes since the incorrect wire was actually back feeding voltage to the switch side of the relay and may have damaged the diodes. If that doesn't work, please sketch out all of your wires and connections since I can't see them all in the pictures (easiest way to do this is to print my wiring diagram PDF and then add/cross out wires to match your wiring.
Connecting the SimpliSafe Video Doorbell to a Digital ChimeView Instructable »