Can I undo a 301 redirect? Will it penalize my ranking?

[naska1990]

I'm in charge of building a website for a company that made a mess.

They own domain xxx.it (xxx is not the real domain, just a placeholder).

Some years ago they 301 redirected xxx.it to xxx.com (they just changed TLDs).

Last year they 301 redirected xxx.com to yyy.com (so, they actually changed domains).

Now, after 13 months, the company failed and the new leadership wants me to undo everything and 301 redirect from yyy.com to xxx.it.

So:

1. 301 redirect is permanent. So, conceptually it's wrong to undo it. What happens if I undo it? Will my ranking be penalized, even if a significant amount of time has passed (13 months)?
2. Will crawlers detect a loop (even if i remove any 301 redirect from xxx.it and theorically break the loop)? Here is the potential loop: xxx.it -> xxx.com -> yyy.com -> xxx.it -> etc...

All of the articles I found on the web are quite old and not clear about this topic, that's why I'm asking this question.

[Dr-Pete]

I know this has been a couple of years, but just a heads up that we've written a more permanent resource about this question on the Moz blog (as it seems to come up periodically):

Can You Reverse A 301 Redirect?

[naska1990]

Thanks for your answer!

Of course i will redirect all the domains to the new one in order to avoid loops.

1. About loops i was referring to the browser cache. As far as i know ome browsers cache also the 301 redirect, so will it be possible that for some users for some time the website will be invisible?
2. So, if i won't be penalized in undoing a 301 redirect, this means that the "permanent" characteristic of 301 is not that strict actually...right?

[Mobilio]

1. There will be some kind of turbulence but if domains are OK (not penalized) then you shouldn't hesitated.

2. This loop is wrong. You should do it xxx.com -> xxx.it; yyy.com -> xxx.it; never enter into redirect loop because this make mess even huge that you expect. Also consider entering HTTP/2 and switching to HTTPS. Because this will be major moving in 2016 year and sooner or later you will do this too.