The former Scotland international trained with East Fife last night, when he was expected to finalise the paperwork his move to the ambitious League One outfit.
The 34-year-old has been without a club since leaving Aberdeen at the end of last season but completed pre-season training with Hearts under the guidance of ex-team-mate Gary Locke.
The former Everton, Sheffield United and Huddersfield Town full-back confessed he was hopeful that a switch to his first club could come off – only for that possibility to be killed off by the SFA’s decision to set a 1 February deadline on the signing restriction that it had been expected would be lifted if, or when, the club emerges from administration.
With a couple of offers south of the border knocked back, the chance to get back playing – with the added possibility of coaching the reserves – at East Fife was one that whetted Naysmith’s appetite. He said: “It looked like something was going to happen at Hearts. There was nothing set in stone but the transfer embargo placed on the club put an end to that.
“I was waiting about to see what was going to happen with that embargo but, once I knew I wasn’t going to get anything there, I had to sort myself out elsewhere.
“I’m fit and ready to go because I did pre-season with Hearts. A couple of things came up in England but I just felt they weren’t right. Then, I got the chance to go over to East Fife and look at the set-up and I spoke to the chairman, who impressed me with where he wants to take the club, so it was a move that appealed to me.”