The 35-year-old spent three-and-a-half seasons at Ibrox, but only played three games for the club.
“When you get the opportunity to go to a massive club like Rangers you don’t turn it down, so I was absolutely delighted,” Webster told BBC Sportsound.
“And then, first training session ended up injured, miss a period of time. All these kind of things and you just end up feeling that you’re chasing your tail thereafter and just seemed to be one thing after another.”
Webster, who began his career with Arbroath, shot to prominence in the wider footballing world in 2006 when he left Heart of Midlothian for Wigan Athletic in a protracted transfer. The defender still had a year left on his contract when he made the move, with Hearts attempting to prevent him leaving.
The complex transfer led to the ‘Webster ruling’ which allows players to walk away from a contract after a fixed period, regardless of the number of years remaining on the contract itself.
However, Webster, who won 28 caps for the national side, returned to Scotland with Rangers on loan in January after playing only four times for the Latics. He had been linked with Rangers in the summer of 2005.
Even though he didn’t play for Rangers that season he was signed on a permanent contract.
Yet, a combination of injury problems and competition within the squad curtailed his long-term involvement at Ibrox.
“An unbelievable club but just not great for me type of thing, in terms of playing and stuff. But in terms of everything else that goes with that football club I couldn’t speak highly enough but really disappointing not to have that opportunity to play.
“But the team was unbelievably successful. You’ve got David Weir, who was the captain and was unbelievable at Rangers, and then you have people like Carlos Cuellar.
“To get an insight into that football club at that period of time with the success they had, as disappointing as it was not playing, probably a bittersweet type of thing.”
Webster had three loan spells away from Rangers, at Bristol City, Dundee United and Hearts before signing permanently for Hearts.
He is currently a free agent following the expiry of his contract at St Mirren.