Cherry eye

A lot of what you ask depends on the breed, the condition and the vet.  Surgery around the eye requires very precise cutting and stitching.  Choose your vet wisely, ask many questions. 
 
I've seen this happen more in cockers and beagles, mostly the smaller long eared breeds.  It also depends on how much of the glad has prolapsed.  In some cases it's alright for the dog to have a minor prolapsed and live without needing surgery to repair it but other times it can impair the dog's vision or be so far protruded that it can actually dry and case some damage to the dogs eye.
 
For the most part surgery to have the gland tucked back in should keep the gland in for the dog's whole life but it sometimes does prolapsed again after surgery.  Much depends on the upkeep of the dog.  If the dog tends to scratch its eye a lot then it can easily cause the gland to pop out.  The owner should really keep a close watch on the dog after surgery.  In some cases the vet may even choose to have the entire gland removed but will only do that if they don#%92t have another option.
 

We just had our bulldog puppy (7 months) cherry eye removed.  After much debate with lots of bulldog people and the breeder and the vet,  we opted to remove not tuck.  Our vet said none of the removals he did have caused "dry eye".
Part of our decision is that bulldogs often die after anathesia and you want to do it as little as possible.  Since the "tuck" might not hold we decided to remove it.  He did a beautiful job and we are so happy.  It was really obstructing her eyesight.

Oh, and he said the recovery time for a tuck was a month vs a day for the removal.  That also made our decision.
 
There were no stiches in the removal.

My moms dog Minnie got the tuck instead of removal because its supposed to be safer or something but it popped back out after a few months and then she got it removed.  She said she should have just got it removed the first time.   The tucking still didnt ever look normal, it was still sorta always red around the corner part of the eye.  Removing did the job tho.

Jason had it done about 4 months ago. i THINK he had it removed... it's hard to say, because although i speak chinese it is hard to talk about medical problems of my dog and understand everything. i'm glad. now i know, what jason had was a cherry eye. he doesn't have any problems whatsoever. the procedure lasted about 10-15 minutes and he only had to get some eyedrops for a few weeks. was really no big deal[]

My dog was done at the age of 6 months. Our Vet and the breeder did not recommend tucking the gland back in place as it will pop out again. Our dogs cherry eye gland was removed and the only long term effect will be that she will need Lubrithal eye drops twice a day and she has got used to having these drops in so there is no problem.