1, 2, and 3 have all been completed with no change. It did work when the folder was slotted manually for each person. Just to be sure I put "materials/meme_gun/1.png" on every possible level of the server, but no luck. Upon refreshing the shooting error I thought I was having seems to be gone so that was probably just lag. Thanks for the work around!

@Mr. Napkins The meme gun doesn't fire unless you hit a player, also unfortunately when there is lag there is a delay in spawning the meme and the gun actually firing.

That error message is perfectly normal and unfortunately a byproduct on how TTT works with custom entities, you can ignore that one.

1. Try creating a materials folder in your server's "garrysmod" folder. So it looks like:
"[your server's main folder]\garrysmod\materials\meme_gun\[whatever name you want].png"

I didn't realise that dedicated servers don't actually have a materials folder by default... my bad. I've updated the mod description to mention this. That alternate directory you shared could work as well, but I haven't tested that.

2. Try to shrink your images, and set them to a square size, both of which can help with a server not forcing players to download images: https://imresizer.com/resize-image-to-500x500-square

(Instead of that website, you can also just use your favourite image editor, like Gimp or Paint .NET, any size 512 x 512 or smaller should work)

3. Try is putting ttt_meme_gun_always_include_default_memes in your server console as a command, this will tell you the actual current value of this setting, and if it is 1, then there might be a problem with your server config.

4. Last if all else fails, just give your players the meme_gun folder directly and have them plop it into their Gmod install's materials folder. You will still need the meme_gun folder on your server as well, this just bypasses the need for the server to send the meme images over automatically.

So, running this on a dedicated server I can't get it to use custom images and it has a weird firing issue were it has to be clicked multiple times before it eventually fires a default meme.

The only thing I see in the console regarding this is:
"Refusing to load ent_meme_gun because it is missing Type and Base keys!"

Also when you say the server materials folder would it be the one under "\gamemodes\terrortown\content\materials"

I am not a professional server/gmod guy, but I can normally wang-jangle it into working, so maybe I'm just being dumb on this one. Either way, any help would be appreciated. In the last 6 years or I've set up TTT three times for my friends and I just wanna say your level of contribution is insanely appreciated. I hope you get thanked as much as you get asked for a sandbox version.

Aces! All seems good now.

@GREENki11erRaBiT I added a fix. Hopefully your internet connection is faster than 1000 ping, else this issue might persist. Thanks for the report!

Amazing mod, one problem. In the folder, whichever picture is first alphabetically has highest priority (I think by default it's the meme of the soccer guy I'm unfamiliar with). This means that whenever you load a new map that meme will always be the first shot, and every shot after that has a 1/3 chance to be that same picture. I renamed a picture to "aa doge" and the problem persisted with that picture instead.

In short, plz help Mr. The Stig.

sandbox version?