Xcode says "Running .. on .. Apple Watch" all the time but never runs. Frustrating

I've had this issue for more than a year now. Sometimes it works, most of the time it doesn't. I can't be the only one experiencing this? The status bar says "Running" but even after half an hour, nothing happens on the Watch. Installing to my iPhone works just fine but as soon as I target the Apple Watch, it gets stuck.

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same problem.

I've had this issue on and off since.... well, since there's been an Apple Watch ;-(

I find debugging an Apple Watch app very frustrasting as I can have a debug setup working as expected, then for an unknown reason, XCODE will take much longer than usual to compile and install the Apple Watch or sometimes cycle through "preparing device" & "installing [app name] watch..." for up to 20 mins (seriously, I use a timer). It will occasionally progress as expected or finally give up with an unhelpful "Unable to install [app name]" dialog.

First, if there are developers who have had dependable debugging experiences with XCODE + Apple Watch, would you please chime with words of encouragement?

Or if anyone has ideas of what to do other than restart XCODE, restart Apple Watch, restart iPhone in some magical order, please share your secret! ;-)

same here, it's very frustrating

I'm sad this seems to be an unsolved problem only Apple can clean up after themselves; I might be even sadder that they removed the "I have this issue too" tag from the forum.

March 2020 and the issue is still there.

Impossible to install a test app on the watch.

It works 1 time ... then doesn't work anymore during hours ...

Me too. Works sometimes and then stops. VERY annoying.
Same here.

Or you wait for ages with this message then suddenly it springs to life before ultimately showing a dialog saying "Unable to Install ... WatchKit App".

Oh for a cable to the watch, or at least the option to prefer WiFi over Bluetooth when both available, but that's another story.

Hey all, I'm curious why this is listed as a Simulator issue... it sounds like you're using Xcode to try to deploy to a physical watch? Or... can someone please clarify exactly what steps you're taking and what you're seeing? Also, if you're hitting this issue, can you please open a feedback assistant issue for this? Please make sure you run sudo sysdiagnose and also xcrun simctl diagnose and attach both resulting files to the feedback assistant so we can take a look at what's going on. Could you also please report back here with the FB number once you do that? Thank you!
the same problem here, pretty annoying scenario, it takes more time trying to run de watch app on the watch than the app developing...

I don't know whether I found a solution, but I resolved the problem for my case.

Normally I would have XCode saying: "Running .. on .. Apple Watch", then it would sometimes say " Unable to install ..".

However, after I removed "Connect via Network" in Window -> Devices and Simulators -> Paired Device the error stopped.

I've been experiencing this issue as well. I go through a cycle of Apple Watch not set up for development. The run destination is not valid for the Running scheme. Error preparing Apple Watch for development. I've jumped through a log of hoops to try to get this to work. I am trying to avoid the ultimate of setting watch up as new watch to get this working.
On occasion the app gets installed on the watch, but never launches, and the debug session never starts.
same problem here.. trying to run App on Apple Watch 3. Magically works one time and not the other hundred. So frustrating and time-consuming.

Restarted everything. Macbook, Watch, Phone nothing works.
Mar 5, 2021: Same problem
I'm having the same issue. More or less exactly as @davenorfleet described.
I'm wondering if it's maybe a faulty watch connection? For some reason I've also been unable to take screenshots on the watch, even if the option is enabled in the watch app. Pressing crown and button simultaniously will even make both watch and iPhone vibrate but there is no screenshot to be found in the camera roll of the iPhone. Does anybody else here experience this?
Mar 11, 2021: Same problem