Help me think this through – “bandaid” roofing repair

I need some help thinking this through. We have been dealing with moisture in our dining room ceiling since the second week of January. Had this section of the ceiling removed end of January by a restoration company. We were hoping it was a one time ice dam, but it leaked again yesterday (with melting snow but a small snow with no ice this time). We’ve got that dried out. The whole restoration process has been financially a lot, and we have a mold-sensitive kiddo so wanting to ensure this doesn’t get wet again.
So here’s where I’d love your advice. This area is by/under a complicated roofline (pan flashing, step flashing, kickout flashing all right there). The 3 roofers we’ve had out don’t know exactly where water is getting in. One did a hose test of this lower portion of roof with all the flashings (there’s a second story above it he didn’t have time to test), and nothing dripped in. But we haven’t hose tested the upper level and my husband and I can’t get up there safely with a hose to do so. All 3 roofers recommended redoing this entire section of roof, since the exact spot is unknown. They’d take out the pan flashing and build a cricket to direct water away from the house better. However, this repair is at least 2 weeks out, likely 3 weeks.
We are expecting several day-long rains next week, each totally around an inch. One roofer said he could come out this Friday, so before the rains, and seal the shingle set back joints, step flashing overlaps and any other conspicuous areas, with caulk. He said the only downside Or this is the cost, as it carries low probability of solving the issue. A second roofer said he’d recommend NOT doing the band-aid fix, as we don’t know where the water is coming in, and the bandaid fix could make matters worse.
Feel like a sitting duck here. Would you do the bandaid roof repair or punt? Thanks for your time.
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Replies
Some roof leaks can be very difficult to diagnose, sometimes it's not the roof, but a wall/roof connection where the wall is leaking due to improper lapping of the layers. It could also be a condensation issue where warm air leaks into a roof or wall and changes to frost only to melt when the temperatures warm. Without knowing the source, you're simply replacing parts hoping you find the issue.
If possible, try to find someone who can help continue the flood test, be sure to not only spray the roof, but also any adjacent wall, especially if that wall has a window. You may also be able to find an energy auditor or someone with a blower door and thermal imaging camera to determine if an air leak might be the source. Often utilities (electric/gas suppliers) have free or reduced rate energy audits for their customers.
Hope this helps,
Randy
The fact that multiple roofers couldn't pinpoint the issue suggests that it may not be a simple flashing or shingle issue. Randy's suggestion of a flood test—including spraying adjacent walls and windows—is a solid one. If possible, hiring someone with thermal imaging or an energy audit specialist could provide additional insight into whether warm air leaks or condensation are contributing factors.
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rhrererehe