diff --git a/CHANGELOG.md b/CHANGELOG.md
index 518b451..a1d8d45 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -25,6 +25,7 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 - Improved accuracy of Selene type definitions, strongly typed arrays are now used where possible
 - Improve error handling and messages for `net.serve`
 - Improve error handling and messages for `stdio.prompt`
+- File path representations on Windows now use legacy paths instead of UNC paths wherever possible, preventing some confusing cases where file paths don't work as expected
 
 ### Fixed
 
diff --git a/Cargo.lock b/Cargo.lock
index 16d810c..0cf1391 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -307,6 +307,12 @@ dependencies = [
  "winapi",
 ]
 
+[[package]]
+name = "dunce"
+version = "1.0.3"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "0bd4b30a6560bbd9b4620f4de34c3f14f60848e58a9b7216801afcb4c7b31c3c"
+
 [[package]]
 name = "encode_unicode"
 version = "0.3.6"
@@ -786,6 +792,7 @@ dependencies = [
  "console",
  "dialoguer",
  "directories",
+ "dunce",
  "futures-util",
  "hyper",
  "hyper-tungstenite",
diff --git a/packages/lib/Cargo.toml b/packages/lib/Cargo.toml
index 274a8ea..fb00df3 100644
--- a/packages/lib/Cargo.toml
+++ b/packages/lib/Cargo.toml
@@ -34,6 +34,7 @@ hyper = { version = "0.14.24", features = ["full"] }
 hyper-tungstenite = { version = "0.9.0" }
 tokio-tungstenite = { version = "0.18.0" }
 mlua = { version = "0.8.7", features = ["luau", "serialize"] }
+dunce = "1.0.3"
 
 [dev-dependencies]
 anyhow = "1.0.69"
diff --git a/packages/lib/src/globals/process.rs b/packages/lib/src/globals/process.rs
index 4a1163e..8f268d3 100644
--- a/packages/lib/src/globals/process.rs
+++ b/packages/lib/src/globals/process.rs
@@ -6,6 +6,7 @@ use std::{
 };
 
 use directories::UserDirs;
+use dunce::canonicalize;
 use mlua::prelude::*;
 use os_str_bytes::RawOsString;
 use tokio::process::Command;
@@ -21,7 +22,7 @@ yield()
 
 pub fn create(lua: &'static Lua, args_vec: Vec<String>) -> LuaResult<LuaTable> {
     let cwd_str = {
-        let cwd = env::current_dir()?.canonicalize()?;
+        let cwd = canonicalize(env::current_dir()?)?;
         let cwd_str = cwd.to_string_lossy().to_string();
         if !cwd_str.ends_with(path::MAIN_SEPARATOR) {
             format!("{cwd_str}{}", path::MAIN_SEPARATOR)
diff --git a/packages/lib/src/globals/require.rs b/packages/lib/src/globals/require.rs
index 5d7d9fe..f04bb30 100644
--- a/packages/lib/src/globals/require.rs
+++ b/packages/lib/src/globals/require.rs
@@ -1,9 +1,10 @@
 use std::{
     env::{self, current_dir},
     fs,
-    path::PathBuf,
+    path::{self, PathBuf},
 };
 
+use dunce::canonicalize;
 use mlua::prelude::*;
 
 use crate::lua::table::TableBuilder;
@@ -35,8 +36,8 @@ pub fn create(lua: &'static Lua) -> LuaResult<LuaTable> {
     }
     // Store the current pwd, and make the functions for path conversions & loading a file
     let mut require_pwd = current_dir()?.to_string_lossy().to_string();
-    if !require_pwd.ends_with('/') {
-        require_pwd = format!("{require_pwd}/")
+    if !require_pwd.ends_with(path::MAIN_SEPARATOR) {
+        require_pwd = format!("{require_pwd}{}", path::MAIN_SEPARATOR)
     }
     let require_info: LuaFunction = lua.named_registry_value("dbg.info")?;
     let require_error: LuaFunction = lua.named_registry_value("error")?;
@@ -53,8 +54,8 @@ pub fn create(lua: &'static Lua) -> LuaResult<LuaTable> {
                 .join(&require_path);
                 // Try to normalize and resolve relative path segments such as './' and '../'
                 let file_path = match (
-                    path_relative_to_pwd.with_extension("luau").canonicalize(),
-                    path_relative_to_pwd.with_extension("lua").canonicalize(),
+                    canonicalize(path_relative_to_pwd.with_extension("luau")),
+                    canonicalize(path_relative_to_pwd.with_extension("lua")),
                 ) {
                     (Ok(luau), _) => luau,
                     (_, Ok(lua)) => lua,