Yes, this was a resounding problem for them that reverberated for several years after. The Federation were certain of their moral and technological superiority that they could not imagine any foe they could not take on readily. And once we became allies, Starfleet became complacent assuming that we, the mighty Klingon Empire would always be there to bail them out of any trouble they might get into. Much like how your NATO countries rely solely on the United States 👀
Discussion
You can actually pinpoint when Starfleet began to decline. The very second this was no longer the duty uniform. It was the Federation version of SS swagger.
We Klingons have a saying: never leave yourself without an Enemy. Starfleet, once Khitomer was signed, really didn't have an enemy. And so Starfleet became captained by scientists, historians, philosophers and my personal favourite, "Humanitarians" -- when the Borg came it was a much needed kick in their complacency. We were delighted to see their military focus redoubled after that. The Klingon Officer Exchange program was initiated to help these our Human allies return to their militaristic and tactical roots. Thinking back on it, we might not have defeated The Dominion without Wolf 359 lighting the spark of change... 👀