Firstly, the Probe Master website lists models 8017S and 8043S as being compatible with a Fluke 87, and it looks like you chose one of those. There's no issue of you going against any recommendations.
I also have a set of Probe Master leads with these connectors at the meter end, and this made me have a look at them. I've got both Fluke 115 and 27 multimeters, and use both Probe Master and Pomona leads with them. I found that for both meters some of the shroud is still visible when they're fully engaged, but the fit is secure.
I took some measurements, and here's what I saw for a Fluke 115:
Probe model | Shroud exposed, start of resistance | Shroud exposed, fully engaged |
Probe Master 8152 | 12mm | 6mm |
Pomona 5519A | 11mm | 3mm |
For a Fluke 27:
Probe model | Shroud exposed, start of resistance | Shroud exposed, fully engaged |
Probe Master 8152 | 9mm | 3mm |
Pomona 5519A | 7mm | 2mm |
What are the measurements for the 87V? If you're seeing 5 to 7mm of further insertion after first resistance you're probably okay.
There's isn't much shroud length left over when these leads are fully engaged in the Fluke 27, and it's likely there are other meters where nothing is left at all. In both the 117 and the 27 the metal part of the socket is recessed quite far in from the front face of the meter, but it seems like they're not nearly as recessed in the 87. Looking at how little shroud is visible for the other leads you've pictured, I wonder if they'd even work for a Fluke 27.
What I think is happening here is that the safety 4mm sockets on multimeters aren't as standard as you'd really expect. Probe Master, Pomona and other manufacturers of test leads are trying to provide a connector that is as compatible with as many meters as possible, so they use a long shroud length.