We are given a nonempty fibrant simplicial set $X$ (a Kan complex) and $v\in X_0$ is any vertex. We are $\alpha\in X_n$ and the map $\alpha:\Delta^n\to X$ is homotopic to $v:\Delta^n\overset{!}{\longrightarrow}\Delta^0\overset{v}{\longrightarrow}X$ relative to $\partial\Delta^n$ (throughout, I will abuse notation as Goerss and Jardine do, by letting $v$ denote any degenerate image of $v$ in any $X_n$).
Let $h:v\simeq\alpha:\Delta^n\times\Delta^1\to X$ be such a homotopy. We have $h\big|_{\partial\Delta^n\times\Delta^1}=v\circ\pi:\partial\Delta^n\times\Delta^1\to\partial\Delta^n\to X$ and $d_i\alpha=v$ for all $0\le i\le n$ by definition of relative homotopy.
The task is to show there exists $\omega\in X_{n+1}$ with boundary $\partial\omega=(d_0\omega,d_1\omega,\cdots,d_n\omega,d_{n+1}\omega)=(v,v,\cdots,v,\alpha)$.
I'm having surprising difficulty with this. I know that we can exploit anodyne extensions to 'fill horns' or similar, e.g. I considered in particular the following: $$(\Delta^1\times\Lambda^n_i)\cup(\partial\Delta^1\times\Delta^n)\hookrightarrow\Delta^1\times\Delta^n\\(\Delta^1\times\partial\Delta^n)\cup(\partial\Delta^1\times\Delta^n)\hookrightarrow\Delta^1\times\Delta^n\\(\Delta^1\times\partial\Delta^n)\cup(\Lambda^1_0\times\Delta^n)\hookrightarrow\Delta^1\times\Delta^n$$To generate new maps $\Delta^1\times\Delta^n\to X$. This was to no avail, because the only sensible maps to put on the components would have to use $h$ somewhere, but $h$ acts trivially or uninterestingly on each such one (e.g. $h$'s restriction to $\partial\Delta^1\times\Delta^n$ is the map $(v,\alpha)$ and this map exists regardless of whether or not $h$ does). In short, I did not see a way to exploit $h$ here.
I might consider similar extensions but with $n+1$ instead of $n$. However, a resulting map $\Delta^1\times\Delta^{n+1}\to X$ does not induce an interesting $\omega:\Delta^{n+1}\to X$, unless I'm mistaken.
Another approach might be to directly use $h$ in some composite $\omega:\Delta^{n+1}\overset{p}{\longrightarrow}\Delta^1\times\Delta^n\overset{h}{\longrightarrow}X$. In order for this to have $d_{n+1}\omega=\alpha$, we need $p(\delta_{n+1})$ equal to $(1,\mathrm{id}_n)$, and for $d_i\omega=v$ for all $i\le n$ we need to guarantee $p(\delta_i)$ is either in $\{0\}\times\Delta^n$ or in $\Delta^1\times\partial\Delta^n$. To make the two compatible, it can only be that $p(\delta_i)$ is in $\Delta^1\times\partial\Delta^n$.
But, examining all possible $(n+1)$-simplices of $\Delta^1\times\Delta^n$, I am fairly sure no such $p$ exists. I don't know what other tools I have at my disposal, so I'd really appreciate any hints or answers.
EDIT: Here is an explicit version of the below answer.
let $h:v\simeq\alpha$ rel. $\partial\Delta^n$. The maps $v\pi:\Delta^1\times\Delta^n\to\Delta^n\to\Delta^0\to X$ and $h:\Delta^1\times\Delta^n$ determine, by a known coequaliser, a unique map $(v\pi,v\pi,\cdots,h):\Delta^1\times\partial\Delta^{n+1}\to X$ since $h$ restricts to $v$ on its boundaries (relative homotopy condition). $v\pi:\{0\}\times\Delta^{n+1}\to\Delta^0\to X$ is compatible with $(v,\cdots,h)$ on the common intersection $\{0\}\times\partial\Delta^n$ since $h$ restricts to $v$ on $\{0\}\times(-)$, so we have a well defined map: $$(\Delta^1\times\partial\Delta^{n+1})\cup(\{0\}\times\Delta^{n+1})\overset{((v\pi,\cdots,v\pi,h),v\pi)}{\longrightarrow}X$$As $X$ is fibrant and the (obvious) inclusion $(\Delta^1\times\partial\Delta^{n+1})\cup(\{0\}\times\Delta^{n+1})\hookrightarrow\Delta^1\times\Delta^{n+1}$ is anodyne, there is an extension of this map to $\psi:\Delta^1\times\Delta^{n+1}\to X$.
If $\iota:\Delta^{n+1}\hookrightarrow\Delta^1\times\Delta^{n+1}$ maps $\sigma\mapsto(1,\sigma)$, then let $\omega:=\psi\circ\iota:\Delta^{n+1}\to X$ (considered also as an $(n+1)$-simplex). If $i\le n$, then $d_i\omega=\omega(\delta_i)=v\pi((1,1))=v$ and $d_n\omega=\omega(\delta_n)=h(1,1)=\alpha(1)=\alpha$ as required.
The first approach should work.
Map one side of the prism $\Delta^1 \times \Delta^{n+1}$ via $h$ and all others via the constant map equal to $v$. Map the button to $v$ as well. This produces a well-defined map from a "cup" to $X$. Extend it to a map $\Delta^1 \times \Delta^{n+1} \to X.$ Restrict to the top of the prism for the desired simplex.