Possibly a good opportunity to ask: On Mac OS X and iTerm2 I've noticed a thing where pasting in commands means they don't get added to the history and using up arrow or search to find them doesn't work. Anyone seen that? It's one of those things that annoys me every time it happens, but I'm always in the middle of a task when it occurs so I never get a chance to figure it out.
Could it be that you're accidentally adding/copying a space at the beginning of the command? I know Linux BASH will ignore the command from history if that's the case, and I think that OSX is similar.
A colon-separated list of values controlling how commands are saved on the history list. If the list of values includes ignorespace, lines which begin with a space character are not
saved in the history list. A value of ignoredups causes lines matching the previous history entry to not be saved. A value of ignoreboth is shorthand for ignorespace and
ignoredups. A value of erasedups causes all previous lines matching the current line to be removed from the history list before that line is saved. Any value not in the above list
is ignored. If HISTCONTROL is unset, or does not include a valid value, all lines read by the shell parser are saved on the history list, subject to the value of HISTIGNORE. The
second and subsequent lines of a multi-line compound command are not tested, and are added to the history regardless of the value of HISTCONTROL.