On Ubuntu 20.04, I have the same problem:
$ execstack -s hello
execstack: dso.c:877: reopen_dso: Assertion `dso->shdr[j].sh_size == 0' failed.
Aborted (core dumped)
sander@witte2004:~/hello-world$ gcc -o hello hello.c
sander@witte2004:~/hello-world$ ./hello
Hello, world!
sander@witte2004:~/hello-world$ ldd hello
linux-vdso.so.1 (0x00007fffe01f4000)
libc.so.6 => /lib/x86_64-linux-gnu/libc.so.6 (0x00007f66793b0000)
/lib64/ld-linux-x86-64.so.2 (0x00007f66795bf000)
sander@witte2004:~/hello-world$ execstack -s hello
execstack: dso.c:877: reopen_dso: Assertion `dso->shdr[j].sh_size == 0' failed.
Aborted (core dumped)
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https://bugs.launchpad.net/bugs/1850861
Title:
execstack --set-execstack<path> Aborted (core dump)
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