• I have tried with the latest version of Docker Desktop
• I have tried disabling enabled experimental features
• I have uploaded Diagnostics
• Diagnostics ID: 165EF212-DB99-4FE1-90A4-E516A309B23F/20210503182644 (taken after restart with port held open)

Expected behavior

A Docker Desktop restart automatically stops all containers and should also disconnect any port listens.

Actual behavior

Instead, with Docker Desktop 3.3.1 (possibly earlier versions as well), a port will still be unavailable (occupied) after a docker desktop restart.

Information

This is easily reproducible on both arm64 and amd64 as below. It does not seem to be a problem on Windows (regular or WSL2, and it does not seem to be a problem on Linux.

• macOS Version: 11.3
• Intel chip or Apple chip: Same behavior with both M1 and Intel, amd64 and arm64
• Docker Desktop Version: 3.3.1

Steps to reproduce the behavior

1. docker run --name nginx -d -p 127.0.0.1:80:80 nginx
2. curl -I http://localhost or nc -vz localhost 80 will show that docker is listening on port 80.
3. Restart docker desktop using the menu item
4. nc -vz localhost 80 will show that the listen port is still occupied. This means that the container cannot be restarted, nor can another container occupy port 80. As a result, docker desktop has to be restarted again to get port 80 cleared.

Removing the container with docker rm nginx does not solve this. You still have to restart docker desktop.

This doesn't seem to happen when binding to 0.0.0.0, so docker run --name nginx -d -p 80:80 nginx doesn't seem to cause this behavior.