Webbe shot a two-under-par 69 at the Adriatic Golf Club in Cervia, bringing his score to nine under for the tournament.
Meanwhile, Germany's Jannik de Bruyn made the most of his recent call-up to the Italian Open as he remained firmly in contention for a first DP World Tour title. De Bruyn shot his second straight 67.
The 24-year-old had been preparing for a tournament on the French Challenge Tour this week before finding himself in the lineup for the Italian event.
“I was playing in France on the Challenge Tour and I got the call on Tuesday saying I could play here,” De Bruyne said.
“A little nervous. I only played nine holes in the practice round, but I enjoyed teeing it up here. Every chance I got was great.”
Wiebe qualified for the Royal Liverpool Open last year by finishing runner-up at the British Masters, but has made just seven cuts in 24 starts since then, with his best finish this season being 41st.
The world No. 568 opened with a 64 to tie for the lead and had three birdies and a bogey in the second round for a 69, good enough for the lead.
“The conditions were really tough,” Wiebe said. “The track started to get pretty firm.”
“You just have to focus. There’s not really one way to hit the ball – I don’t want to say mail it out – but you have to be mentally prepared from the start because of how tricky the wind is.
“You could say I played better today than I did yesterday. Of course, you can tell by the score, but I thought I played a little sharper today.”
Sweden's Marcus Kinhult lost a play-off at the KLM Open on Sunday, leaving South Africa's Brandon Stone, Spain's Adrian Otaegui and Denmark's Sebastian Friedrichsen two shots off the lead at seven under.
Scotland's Richie Ramsay and the English trio of Dan Bradbury, Andrew Johnston and Callum Shinkwin led the British Challenge team at five under.
