Not enough random bytes

I got a particularly entertaining error message while using the GPG key gen over ssh. 

Not enough random bytes available.  Please do some other work to give
the OS a chance to collect more entropy! (Need 284 more bytes)

I found a way to watch the entropy generated. I tried some strategies like downloading, compiling cating large files, listing recursively the home,  but the entry number kept "getting eaten." The highest I got it to was 50. 

watch cat /proc/sys/kernel/random/entropy_avail

After deciding that I might as well list the entire root, which is 2 terabytes, I made progress.

Not enough random bytes available.  Please do some other work to give

the OS a chance to collect more entropy! (Need 92 more bytes)

+++++

Not enough random bytes available.  Please do some other work to give

the OS a chance to collect more entropy! (Need 115 more bytes)