What’s the best way to fix:
The nails have lost their grip.
Your railing and attachment is far too flimsy. Take a gander at some other railings that seem to work.
Dik
The other side works. It’s identical.
It shouldn’t… if it does, then it is not likely constructed ‘exactly’ as the failed one. The railing still looks flimsy and not capable of withstanding most rail loadings.
Dik
The top bent member might have a permanent warp in it causing extra stress on the nails. Could have been installed with the warp.
Try replacing the top member, and you might try using screws into the side grain.
No end grain screwing into the post. End grain screwing or nailing is weaker than side grain.
Also, you should stop using the end of the top member to open your beers.
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If you want to try resecuring the existing rail, pull it into place with a ratchet strap rather than trying to use the fasteners to do both “pull closed” and “hold closed”.
Options for “hold closed” in order of increasing aggressiveness:
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Couple of long woodscrews into the side of the long rail that lies underneath the handrail. Try to offset the screws slightly off the centreline or put them in slightly skew to reduce the risk of their splitting the rail.
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Clearance hole in the handrail, with a shallow counterbore at the top; corresponding pilot hole in the upright post and then secure with a nice long and fat coach screw and washer.
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Clearance hole in both handrail and post, with a shallow counterbore in the handrail and an intercepting cross-bore in the post; Put a barrel nut into the crossbore and secure with a bolt and washer.
Some really good responses. Thanks!
I lifted up the loose end until the two 10d ring shank nails popped out of their existing holes. They sprung up and landed about 1/4" above the existing holes and at a significantly different angle (virgin wood even though it’s end grain). Since I think the initial installation held 10 years (we bought 1 year ago), I decided to hammer them in at the new position/angle and see if/how long it holds. If it doesn’t, I think I’ll try zuesfaber’s #1 first (the wood is in good shape), but if that doesn’t hold, go with msquared’s new wood approach.
I suspect I’ll have to revisit/update this within a year or so. It’ll probably pull free again, but lets see. I may get lucky.
I’d add one or two long (maybe 6") screws down into the post. Yes, end grain doesn’t hold as well, but it will hold if you go deep enough. Your local big box store should have a good selection of timber fasteners that will fill the bill.
You have to go deeper and put a nut on the end. 
You might want to revisit the connections.
Dik