Annan struggled with injuries in his first spell with Boro before joining the Brewers.
The former Hull City winger rejoined Boro as one of a host of Albion players snapped up by boss John Deacey in the summer, but has decided to exit the Flamingo Land Stadium club to join up with Taddy boss Curtis Woodhouse.
Albion boss Woodhouse said: “Delighted to welcome Will Annan back to Tadcaster Albion. He’s a player I’ve liked for a while and first caught my eye when he was at Hull City.
"He will add some real quality and competition to our squad and it’s a really good signing for us.
”We have a really good vibe in the dressing room at the moment, everybody pulling in the same direction and Will fits in well with the principles I like and I’m sure once he finds his feet and settles into how we want to play he will make a big impact for us.”