Thanks for the suggestion. Does this link show me how to use the logs. Maybe that is what I have been missing with my trouble shooting!!!
What type of device is the family room clock?
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Can you also share:
- Hub version? C4/C5/C7/C8?
- Hub Platform Version? (Settings>Details)
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@user3425 - can you address @sburke781's question? Thanks!
Also, how is your hub's IP address assigned? Via a DHCP reservation? Can you confirm that hub's address is still 192.168.1.93 when the rule stops working?
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My guess is a Sonos/Ikea speaker without a router DHCP reservation....
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Thanks everyone for your help. I used the logs to find that it was sending the command but the chromecast app wasn't working properly. I think I fixed it. Thanks!
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It's Millah-time! Or...maybe this? 
The problem is back. I created this for testing and it works fine for about 24 hours or so and the only way to get it working again is to reboot the hub.. Any ideas? If I go back to a very old firmware, it keeps working without reboot, so what ever changes were made in the firmware screw this function up.
Turn on all available logging for the rule, and share that here the next time it fails to run.
Maybe some info found there there will help. 
I think it has to do where it's going. I am sending it to the google mini. some how for some reason it works for about 1 day if I reboot the hub. sometype of connection problem with the google devices?
I don't have experience using my Google devices that way, so can't speak to the reliability. When it fails from the hub, does it also fail if you send the action from your browser on your PC?
That, I don't know how to do.
It has something to do with this integration. I think it fails to work after setting for a while, I am not sure how to fix it.
I should have asked earlier - Hub version (C5, C7, C8?) and platform version? Current Hub platform version is 2.3.8.134. If you aren't on that version you should update.
I use the Chromecast integration multiple times every day for door/window open announcements, goodnight tasks, etc., and it always works unless I'm having problems w/my network, GH can't connect for some reason. Not sure why it would not be equally reliable for you.
There is a process to re-initialize your Chromecast via rule - See the example below. You can set it to run as often as it seems to need in your environment - below would run the Initialize daily at 7am.
Start a new rule and set the Trigger to something like running daily in the morning.
For the Action choose the "...Run Custom Action" type:
Set as below:
Rule should look like this:
See if that helps.
Also, when asking for help is helpful if you post your hub version (C5, C7, C8) and current Platform Version you're running on the hub. 
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It is a C-7. It worked great for almost a year then one update it was the way it is now. If I reboot the hubitat it will work for a little while then quit again.
The Chromecast integration has always had some reliability issues for some users. I am not sure if the root cause has ever been determined. But, for most users, simply running the Initialize() command on the device seems to get things working again. The Initialize() command is run automatically each time the hub is rebooted.
Thus, @danabw's advice to use a rule to run Initialize() every day makes a lot of sense, to try and keep the connection between the HE and the Google Home device alive.
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I was wondering if that would be possible. I will look for it on his postings. Thanks!!!
Would you have a link to that?
Just above in this topic.
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