Wait for the server in PuTTy

Is there any run switch or configuration setting in PuTTY for Windows that instead of showing me this screen:

Would rather ask me a question, if I want to wait some time and try to reestablish the same connection as previously? I've seen simiar solutions many times in many other apps.

I am doing some research on my RaspberryPi and so I must reboot it often. Sometimes even 20-30 times per hour. It drives me crazy that each time I click OK in above dialog box, PuTTy quits completely and I have to:

• Hit Win+M to minimise all the apps
• Look for the PuTTy's icon on my desktop or hit Start, type Put and hit Enter
• Double click session settings in the list again to start up the same session again

Is there any way to prevent this, make this a little bit more automated etc.?

EDIT: My question is not a duplicate of this question because all answers provided there talks about different software (a large number of PuTTy's forks). While I ask specifically about "core" / "original" PuTTy. And for that reason only the answer given below seems valid.

Solution 1:

Make sure your PuTTY connection profile has:

Close window on exit:
(*) Only on clean exit

(If this doesn't help, choose "Never.")

With this option selected, the window will remain open so you can Ctrl+Right-click it and select D "Duplicate Session" or even R "Restart Session" every time the connection is closed.

To start PuTTY quickly, press WinR and enter putty. You can append the hostname to the command (e.g. putty root@pi) or load a saved profile (e.g. putty -load "My Raspberry").