Just to add on @intelligenti's answer. Say that you are pulling the top strap sideways (with both hands) so that it stays parallel to its initial position.
As you pull, the top part of the cylinder will "produce" slack because a chord of the circle is always shorter than the diameter. In the same time, the side will "consume" slack because the strap is now oblique instead of vertical. Which one wins?
Using the notation of @intelligenti with $r = 1$ and $h = 1$, the top section will produce slack similar to a cosine:
$$
1-\cos\alpha
$$

The side will consume slack proportional to:
$$
\sqrt {1 + \alpha^2 }-1
$$

Those two functions looks very similar. Here they are on the same graph.

Zooming in, the blue curve is always above the green curve (on the range $0<\alpha<\pi/2)$, so theoretically for $h=r$ it will slip.
Here is a 3D plot with $\alpha$ on the x axis and h on the y axis ($r=1$). Vertically is the amount of slack in total (top - side).

From this plot we can see that for $h<1$, the surface dips below 0 (blue/purple part). More slack is taken than given: it holds tight.
For $h>1$, the surface is above 0 (green part): it slips.
Some part of the surface looks funny. Here it is with $h=0.9$ (slightly shorted than the radius):

The curve dips below 0 before getting back up. This shape is normally safe ($h<1$), however if the strap is even slightly elastic or you misplace it, it can reach a point were it will completely slip off.
Shapes below $h=0.74$ are completely safe:

The curve never gets above 0 before $\pi/2$. You can strap them as you want (even close to the border): they will not slip.