Bailey will pitch for the PawSox on Wednesday and Thursday, barring any setbacks. He tossed an inning for Double-A Portland on Sunday, allowing one run and striking out two.
"I feel good, it was nice to get back out there and I feel pretty normal today, so I'm just looking forward to the next step in the program and getting back," said Bailey, who had right thumb surgery the day before the 2012 season began.
The right-hander reached 94 mph with his fastball on Sunday and also used his cutter and curveball. He still has a few more rehab outings left before the Red Sox will be ready to activate him. Bailey has not pitched for Boston this year.
"Just got to knock off the rust, but after yesterday, I'm very confident that I'll be here soon and I definitely took a lot of positives out of it," Bailey said before Monday's game against the Rangers. "This whole year has been a snail's pace."
Fellow reliever Rich Hill is getting closer to a rehab assignment of his own. The left-hander threw a bullpen session at Fenway Park on Monday, and he could head out to Florida to join the Gulf Coast League Red Sox later this week when Boston begins a 10-game road trip on Thursday.
"His mound work has been really good, and we're close to getting him to Florida to pitch in a game," said Red Sox manager Bobby Valentine. "And that might be as soon as we leave. It might be batting practice first there and then a game."
Hill has been on the 60-day disabled list since June 10 with a strained left elbow.