Suppose I have a $k$ sided die with the numbers $1,2,\ldots,k$ on each side, and that I roll it $n$ times ($n<k$).
What is the probability that there exists an $m\leq n$, so that $m$ of the $n$ rolls lie in the set $\{1,2,\ldots,m-1\}$?
If a closed form in terms of $k,n$ cannot be easily found, a recursion would be equally useful, so it can be more easily calculated.
I have tried calculating this for specific values of $n$ and $k$, but it is difficult, because the two events corresponding to distinct values of $m$ are not mutually exclusive, so you can't just calculate the probability of the event occurring for each value of $m\leq n$, and add them up. This means that copious use of the Principle of Inclusion-Exclusion is required, and it gets messy very quickly.
I fiddled with this after the false-start of missing the $-1$ on $m-1$ for the set.
It appears that the desired result is $S/k^n$, where $S$ is the $(n-1)_{\text{th}}$ element of the $k_{\text{th}}$ row of $A099614$.
So, e.g,. for a six sided die rolled 4 times, $89/432$ results.
The following Mathematica snippet calculates this directly.
One can also use WolframAlpha (snip the code to the right of ":=" and replace symbols with values).
I have not found a more direct method to generate the numerator, I'm sure one probably exists.
Here's a quick plot of the calculated results against a simulation check for a 20-sided die rolled 2 to 19 times.