diff --git a/.vscode/settings.json b/.vscode/settings.json
index 8361ab3..19288c5 100644
--- a/.vscode/settings.json
+++ b/.vscode/settings.json
@@ -2,8 +2,6 @@
 	// Luau - disable Roblox features, enable Lune typedefs & requires
 	"luau-lsp.sourcemap.enabled": false,
 	"luau-lsp.types.roblox": false,
-	"luau-lsp.types.definitionFiles": ["luneTypes.d.luau"],
-	"luau-lsp.types.documentationFiles": ["luneDocs.json"],
 	"luau-lsp.require.mode": "relativeToFile",
 	// Luau - ignore type defs file in docs dir and dev scripts we use
 	"luau-lsp.ignoreGlobs": [
diff --git a/packages/cli/src/cli.rs b/packages/cli/src/cli.rs
index ff4c72e..c1f8189 100644
--- a/packages/cli/src/cli.rs
+++ b/packages/cli/src/cli.rs
@@ -1,12 +1,18 @@
-use std::process::ExitCode;
+use std::{
+    borrow::BorrowMut,
+    collections::HashMap,
+    path::{Path, PathBuf},
+    process::ExitCode,
+};
 
 use anyhow::{Context, Result};
 use clap::{CommandFactory, Parser};
+use serde_json::Value as JsonValue;
 
 use include_dir::{include_dir, Dir};
 use lune::Lune;
 use tokio::{
-    fs::read as read_to_vec,
+    fs::{self, read as read_to_vec},
     io::{stdin, AsyncReadExt},
 };
 
@@ -81,6 +87,7 @@ impl Cli {
         self
     }
 
+    #[allow(clippy::too_many_lines)]
     pub async fn run(self) -> Result<ExitCode> {
         // List files in `lune` and `.lune` directories, if wanted
         // This will also exit early and not run anything else
@@ -124,7 +131,43 @@ impl Cli {
                 return Ok(ExitCode::FAILURE);
             }
             if self.setup {
-                generate_typedef_files_from_definitions(&TYPEDEFS_DIR).await?;
+                let generated_paths =
+                    generate_typedef_files_from_definitions(&TYPEDEFS_DIR).await?;
+                let settings_json_path = PathBuf::from(".vscode/settings.json");
+                let message = match fs::metadata(&settings_json_path).await {
+                    Ok(meta) if meta.is_file() => {
+                        if try_add_generated_typedefs_vscode(&settings_json_path, &generated_paths).await.is_err() {
+							"These files can be added to your LSP settings for autocomplete and documentation."
+						} else {
+							"These files have now been added to your workspace LSP settings for Visual Studio Code."
+						}
+                    }
+                    _ => "These files can be added to your LSP settings for autocomplete and documentation.",
+                };
+                // HACK: We should probably just be serializing this hashmap to print it out, but
+                // that does not guarantee sorting and the sorted version is much easier to read
+                let mut sorted_names = generated_paths
+                    .keys()
+                    .map(ToString::to_string)
+                    .collect::<Vec<_>>();
+                sorted_names.sort_unstable();
+                println!(
+                    "Typedefs have been generated in the following locations:\n{{\n{}\n}}\n{message}",
+                    sorted_names
+                        .iter()
+                        .map(|name| {
+                            let path = generated_paths.get(name).unwrap();
+                            format!(
+                                "    \"@lune/{}\": \"{}\",",
+                                name,
+                                path.canonicalize().unwrap().display()
+                            )
+                        })
+                        .collect::<Vec<_>>()
+                        .join("\n")
+                        .strip_suffix(',')
+                        .unwrap()
+                );
             }
         }
         if self.script_path.is_none() {
@@ -172,3 +215,29 @@ impl Cli {
         })
     }
 }
+
+async fn try_add_generated_typedefs_vscode(
+    settings_json_path: &Path,
+    generated_paths: &HashMap<String, PathBuf>,
+) -> Result<()> {
+    // FUTURE: Use a jsonc or json5 to read this file instead since it may contain comments and fail
+    let settings_json_contents = fs::read(settings_json_path).await?;
+    let mut settings_changed: bool = false;
+    let mut settings_json: JsonValue = serde_json::from_slice(&settings_json_contents)?;
+    if let JsonValue::Object(settings) = settings_json.borrow_mut() {
+        if let Some(JsonValue::Object(aliases)) = settings.get_mut("luau-lsp.require.fileAliases") {
+            for (name, path) in generated_paths {
+                settings_changed = true;
+                aliases.insert(
+                    format!("@lune/{name}"),
+                    JsonValue::String(path.canonicalize().unwrap().to_string_lossy().to_string()),
+                );
+            }
+        }
+    }
+    if settings_changed {
+        let settings_json_new = serde_json::to_vec_pretty(&settings_json)?;
+        fs::write(settings_json_path, settings_json_new).await?;
+    }
+    Ok(())
+}
diff --git a/packages/cli/src/gen/mod.rs b/packages/cli/src/gen/mod.rs
index 64551df..a0acfa0 100644
--- a/packages/cli/src/gen/mod.rs
+++ b/packages/cli/src/gen/mod.rs
@@ -1,4 +1,4 @@
-use std::collections::HashMap;
+use std::{collections::HashMap, path::PathBuf};
 
 use anyhow::Result;
 use include_dir::Dir;
@@ -15,7 +15,9 @@ pub async fn generate_gitbook_dir_from_definitions(dir: &Dir<'_>) -> Result<()>
     gitbook_dir::generate_from_type_definitions(definitions).await
 }
 
-pub async fn generate_typedef_files_from_definitions(dir: &Dir<'_>) -> Result<()> {
+pub async fn generate_typedef_files_from_definitions(
+    dir: &Dir<'_>,
+) -> Result<HashMap<String, PathBuf>> {
     let definitions = read_typedefs_dir(dir)?;
     typedef_files::generate_from_type_definitions(definitions).await
 }
diff --git a/packages/cli/src/gen/typedef_files.rs b/packages/cli/src/gen/typedef_files.rs
index 03062ca..33453bf 100644
--- a/packages/cli/src/gen/typedef_files.rs
+++ b/packages/cli/src/gen/typedef_files.rs
@@ -1,4 +1,4 @@
-use std::{collections::HashMap, fmt::Write};
+use std::{collections::HashMap, fmt::Write, path::PathBuf};
 
 use anyhow::{Context, Result};
 use directories::UserDirs;
@@ -13,7 +13,7 @@ const GENERATED_COMMENT_TAG: &str = "--!strict";
 #[allow(clippy::too_many_lines)]
 pub async fn generate_from_type_definitions(
     api_reference: HashMap<String, DefinitionsTree>,
-) -> Result<()> {
+) -> Result<HashMap<String, PathBuf>> {
     let mut dirs_to_write = Vec::new();
     let mut files_to_write = Vec::new();
     // Create the typedefs dir in the users cache dir
@@ -21,7 +21,7 @@ pub async fn generate_from_type_definitions(
         .context("Failed to find user home directory")?
         .home_dir()
         .join(".lune")
-        .join("typedefs")
+        .join(".typedefs")
         .join(env!("CARGO_PKG_VERSION"));
     dirs_to_write.push(cache_dir.clone());
     // Make typedef files
@@ -36,8 +36,8 @@ pub async fn generate_from_type_definitions(
             category_name.to_lowercase(),
             env!("CARGO_PKG_VERSION")
         )?;
-        write_tree(&mut contents, category_name, category_tree)?;
-        files_to_write.push((path, contents));
+        write_tree(&mut contents, category_name.to_string(), category_tree)?;
+        files_to_write.push((category_name.to_lowercase(), path, contents));
     }
     // Write all dirs and files only when we know generation was successful
     let futs_dirs = dirs_to_write
@@ -45,12 +45,15 @@ pub async fn generate_from_type_definitions(
         .map(create_dir_all)
         .collect::<Vec<_>>();
     let futs_files = files_to_write
-        .drain(..)
-        .map(|(path, contents)| write(path, contents))
+        .iter()
+        .map(|(_, path, contents)| write(path, contents))
         .collect::<Vec<_>>();
     try_join_all(futs_dirs).await?;
     try_join_all(futs_files).await?;
-    Ok(())
+    Ok(files_to_write
+        .drain(..)
+        .map(|(name, path, _)| (name, path))
+        .collect::<HashMap<_, _>>())
 }
 
 fn make_return_table_item(item: &DefinitionsItem) -> Result<String> {