I've also tried a sim pull

And network settings reset 

Is your data on?

When long sms become mms, you need your data turned on to send and receive.

Here is a link that discuss about sms and MMS.

Have you tried sending a picture message? Does the picture message send? 

Hello! Data is on and picture will send. Short message sends too. Anything long just sits on sending 

Have you tried seeing if some setting on your messaging app is blocking the sending of longer messages? The fact MMS (picture) sends but not long texts is weird.  

No settings like that that I can see. Tried from a different sms app same issue

OK then, try clearing your messaging app's cache and data. To do this on an Android phone, go to Settings > Apps > Your messaging app > Storage > Clear Cache and Clear Data. On an iPhone, go to Settings > General > iPhone Storage > Your messaging app > Offload App.

Additonally try your SIM card in another phone to see if it’s a phone related issue. 

Tried everything. Got ahold of tech support who told me that the max output is approx 360 characters that will be split into multiple messages. 

The weird part is that I've sent longer texts than that before without issue as recently as two days ago and it just suddenly stopped working but I was basically told to just accept the limitations...

I find it pretty weird too as I’m clearly sending texts longer then 360 characters...

Is there a koodo rep here that can help go deeper?

I could flag one so he can take a look at it. I’ll do it as we speak.

Fixed it!!

How did you manage to fix it? 

I contacted Samsung and they fixed it somehow. Not sure what they did but it seems like it was a phone issue afterall. I'm my defense the other phone I tried was also a Samsung lol

So you changed phones and that’s what caused the issue? These details are important for us to better help you out :)