It started raining badly as I was driving today and noticed a new quirk in my 98 XJ. On the drivers side to the left of the rear view mirror water started leaking from the headliner, pictures are attached for clarification. How can I fix this issue?

 

Similar issue with my '00. But between the passenger side visor and the mirror.
Quick remove and replace of the windshield fixed that all up. Used a new molding.
Thing is if that is the problem and you remove the windshield no telling what you might find under there.
If water seeped in there long enough could have started to rot the channel the windshield goes in.

 

Isnt the process to remove the windshield and apply new molding and weathering a difficult task? I checked youtube and it seems pretty straight forward, downside is I don't have a garage

 

Oh I had mine professionally done.
It just so happened that I was having so surface rust issues on the hood and roof being handled by my body guy.
So I asked him to deal with the windshield. So he had his glass guy, who is now my glass guy (LOL), do it.
My point is if there was something bad going on under the rubber molding my body guy could have dealt with it right then and there.
Fortunately is was just a remove and replace so.....

 

I did mine. It's really not that difficult. You do need a special tool to cut the existing urethane, but that can be as simple (and inexpensive) as a special wire you can find on Amazon.

Doing it yourself allows you to take your time and clean up the rust. Although, once you get in there, you might find a job for a body shop. Depends how bad it is.

See here, here, and here for more info. Especially here, for a good picture of what you are dealing with.

What you MUST understand is that the rubber "seal" around the windshield is NOT a seal;. It is PURELY cosmetic. The urethane glue is the seal. Once it has failed, there is no fixing it without removing the windshield. The other thing to know is that the urethane rarely fails. It's almost always rust.

One option is to remove it yourself, fix the rust, then pay a pro to reinstall it.

 

Just so that you're not going into this with rose tinted glasses, this was the cause of my headliner leak. Mine had been sat for 7/8 years before I got it back on the road, so if you've had it for a while and it's only just started leaking, it probably won't look like this.

Oh and if you do need to do some rust repair, don't do what I did and regret it later down the line, remove the headliner and not just snap it out of the way.