When you see the Timed out waiting for connection to Loggregator (wss://doppler.bosh-lite.com:4443) error while pushing an App after you upgraded your CF, you may want to quickly try the following fixes.

1) Check your cf_cli version, if it is older version, please update it the latest version (v6.25+ works for me).
2) Log out you cf api and re login.
3) Push your app again.

Here is why. If you were using older version of CF and its cli and logged in your cf while the default port is 4443, then in your .cf/config.json, it will save DopplerEndPoint as wss://doppler.cf_base_domain:4443. Now you upgraded the newer version CF which is using 443 as default port for DopplerEndPoint. Since your cf_cli is not updated, when you logged in to your cf, it may fail to update DopplerEndPoint in your .cf/config.json file.

If you are using older version CF which is still using 4443 as default port for Loggregator. You can try the following normal methods.

Run cf logs app_name --recent to see more detailed error messages.

Connected, dumping recent logs for app cf-env in org system / space test as admin...

FAILED  
Error dialing trafficcontroller server: Get https://doppler.bosh-lite.com:4443/apps/076960f2-71ff-463d-812b-b419159077e4/recentlogs: dial tcp 10.244.0.34:4443: getsockopt: connection refused.  
Please ask your Cloud Foundry Operator to check the platform configuration (trafficcontroller endpoint is wss://doppler.bosh-lite.com:4443).  

bosh ssh to the doppler VM, run monit summary to see if all the processes are running, check the logs on the doppler vm, list ports that are listening and using nc -v localhost port to test the networking. You may find useful info to help debug from there.