diff --git a/.vs/launch.vs.json b/.vs/launch.vs.json
index 15691e1583..0b5a8576a0 100644
--- a/.vs/launch.vs.json
+++ b/.vs/launch.vs.json
@@ -141,13 +141,6 @@
       "name": "REPL - Jak 2",
       "args": ["--user-auto", "--game", "jak2"]
     },
-    {
-      "type": "default",
-      "project": "CMakeLists.txt",
-      "projectTarget": "goalc.exe (bin\\goalc.exe)",
-      "name": "REPL - Auto Listen",
-      "args": ["--user-auto", "--auto-lt"]
-    },
     {
       "type": "default",
       "project": "CMakeLists.txt",
diff --git a/Taskfile.yml b/Taskfile.yml
index 08844a2bd1..17fd4dcb8c 100644
--- a/Taskfile.yml
+++ b/Taskfile.yml
@@ -68,9 +68,6 @@ tasks:
         msg: "Couldn't locate compiler executable in '{{.GOALC_BIN_RELEASE_DIR}}/goalc'"
     cmds:
       - "{{.GOALC_BIN_RELEASE_DIR}}/goalc --user-auto --game {{.GAME}}"
-  repl-lt:
-    cmds:
-      - "{{.GOALC_BIN_RELEASE_DIR}}/goalc --auto-lt --user-auto --game {{.GAME}}"
   format:
     desc: "Format code"
     cmds:
diff --git a/common/CMakeLists.txt b/common/CMakeLists.txt
index adf0c5e3ee..24b25a6324 100644
--- a/common/CMakeLists.txt
+++ b/common/CMakeLists.txt
@@ -19,11 +19,12 @@ add_library(common
         goos/PrettyPrinter2.cpp
         goos/Reader.cpp
         goos/TextDB.cpp
-        goos/ReplUtils.cpp
+        repl/config.cpp
+        repl/util.cpp
         log/log.cpp
         math/geometry.cpp
-        nrepl/ReplClient.cpp
-        nrepl/ReplServer.cpp
+        repl/nrepl/ReplClient.cpp
+        repl/nrepl/ReplServer.cpp
         type_system/defenum.cpp
         type_system/deftype.cpp
         type_system/state.cpp
diff --git a/common/cross_sockets/XSocketClient.cpp b/common/cross_sockets/XSocketClient.cpp
index 025b445a7e..25aff3e657 100644
--- a/common/cross_sockets/XSocketClient.cpp
+++ b/common/cross_sockets/XSocketClient.cpp
@@ -12,7 +12,7 @@
 #include <WinSock2.h>
 #include <WS2tcpip.h>
 #endif
-#include "common/nrepl/ReplServer.h"
+#include "common/repl/nrepl/ReplServer.h"
 
 #include "third-party/fmt/core.h"
 // clang-format on
diff --git a/common/goos/Interpreter.cpp b/common/goos/Interpreter.cpp
index bc1b927347..222635cf58 100644
--- a/common/goos/Interpreter.cpp
+++ b/common/goos/Interpreter.cpp
@@ -160,7 +160,7 @@ HeapObject* Interpreter::intern_ptr(const std::string& name) {
 /*!
  * Display the REPL, which will run until the user executes exit.
  */
-void Interpreter::execute_repl(ReplWrapper& repl) {
+void Interpreter::execute_repl(REPL::Wrapper& repl) {
   want_exit = false;
   while (!want_exit) {
     try {
diff --git a/common/goos/Interpreter.h b/common/goos/Interpreter.h
index cb78fc30d5..a58dbdb61c 100644
--- a/common/goos/Interpreter.h
+++ b/common/goos/Interpreter.h
@@ -16,7 +16,7 @@ class Interpreter {
  public:
   Interpreter(const std::string& user_profile = "#f");
   ~Interpreter();
-  void execute_repl(ReplWrapper& repl);
+  void execute_repl(REPL::Wrapper& repl);
   void throw_eval_error(const Object& o, const std::string& err);
   Object eval_with_rewind(const Object& obj, const std::shared_ptr<EnvironmentObject>& env);
   bool get_global_variable_by_name(const std::string& name, Object* dest);
diff --git a/common/goos/Reader.cpp b/common/goos/Reader.cpp
index ce86dd29bf..7c77d4dae7 100644
--- a/common/goos/Reader.cpp
+++ b/common/goos/Reader.cpp
@@ -11,9 +11,8 @@
 
 #include "Reader.h"
 
-#include "ReplUtils.h"
-
 #include "common/log/log.h"
+#include "common/repl/util.h"
 #include "common/util/FileUtil.h"
 #include "common/util/FontUtils.h"
 
@@ -195,7 +194,7 @@ bool Reader::is_valid_source_char(char c) const {
 /*!
  * Prompt the user and read the result.
  */
-std::optional<Object> Reader::read_from_stdin(const std::string& prompt, ReplWrapper& repl) {
+std::optional<Object> Reader::read_from_stdin(const std::string& prompt, REPL::Wrapper& repl) {
   // escape code will make sure that we remove any color
   std::string prompt_full = "\033[0m" + prompt;
 
diff --git a/common/goos/Reader.h b/common/goos/Reader.h
index 9dd725ab97..32b51f075b 100644
--- a/common/goos/Reader.h
+++ b/common/goos/Reader.h
@@ -16,10 +16,9 @@
 #include <unordered_map>
 #include <utility>
 
-#include "ReplUtils.h"
-
 #include "common/goos/Object.h"
 #include "common/goos/TextDB.h"
+#include "common/repl/util.h"
 #include "common/util/Assert.h"
 
 namespace goos {
@@ -74,7 +73,7 @@ class Reader {
   Object read_from_string(const std::string& str,
                           bool add_top_level = true,
                           const std::optional<std::string>& string_name = {});
-  std::optional<Object> read_from_stdin(const std::string& prompt, ReplWrapper& repl);
+  std::optional<Object> read_from_stdin(const std::string& prompt, REPL::Wrapper& repl);
   Object read_from_file(const std::vector<std::string>& file_path, bool check_encoding = false);
   bool check_string_is_valid(const std::string& str) const;
 
diff --git a/common/goos/ReplUtils.h b/common/goos/ReplUtils.h
deleted file mode 100644
index 199bd0444e..0000000000
--- a/common/goos/ReplUtils.h
+++ /dev/null
@@ -1,37 +0,0 @@
-#pragma once
-
-#include <functional>
-#include <string>
-#include <vector>
-
-#include "third-party/replxx/include/replxx.hxx"
-
-using Replxx = replxx::Replxx;
-
-class ReplWrapper {
-  Replxx repl;
-
- public:
-  ReplWrapper() {}
-  Replxx& get_repl() { return repl; }
-  void init_default_settings();
-
-  // Functionality / Commands
-  void clear_screen();
-  void print_to_repl(const std::string_view& str);
-  void print_welcome_message();
-  void set_history_max_size(size_t len);
-  const char* readline(const std::string& prompt);
-  void add_to_history(const std::string& line);
-  void save_history();
-  void load_history();
-  void print_help_message();
-  std::pair<std::string, bool> get_current_repl_token(std::string const& context);
-
-  std::vector<std::string> examples{};
-  using cl = Replxx::Color;
-  std::vector<std::pair<std::string, cl>> regex_colors{};
-
- private:
-  replxx::Replxx::key_press_handler_t commit_text_action(std::string text_to_commit);
-};
diff --git a/common/repl/config.cpp b/common/repl/config.cpp
new file mode 100644
index 0000000000..ea106405e6
--- /dev/null
+++ b/common/repl/config.cpp
@@ -0,0 +1,95 @@
+#include "config.h"
+
+#include "common/versions.h"
+
+#include "third-party/fmt/core.h"
+
+namespace REPL {
+void to_json(json& j, const Config& obj) {
+  j = json{
+      {"numConnectToTargetAttempts", obj.target_connect_attempts},
+      {"asmFileSearchDirs", obj.asm_file_search_dirs},
+      {"keybinds", obj.keybinds},
+  };
+}
+
+void from_json(const json& j, Config& obj) {
+  if (j.contains("numConnectToTargetAttempts")) {
+    j.at("numConnectToTargetAttempts").get_to(obj.target_connect_attempts);
+  }
+  if (j.contains("asmFileSearchDirs")) {
+    j.at("asmFileSearchDirs").get_to(obj.asm_file_search_dirs);
+  }
+  if (j.contains("appendKeybinds")) {
+    j.at("appendKeybinds").get_to(obj.append_keybinds);
+  }
+  if (j.contains("keybinds")) {
+    std::vector<KeyBind> keybinds = j.at("keybinds");
+    if (!obj.append_keybinds) {
+      obj.keybinds = keybinds;
+    } else {
+      // append the keybinds
+      // - start with the provided ones
+      // - skip ones from the default set if they have the same key + modifier combination
+      for (const auto& default_bind : obj.keybinds) {
+        // check if it's a duplicate bind
+        bool duplicate = false;
+        for (const auto& new_bind : keybinds) {
+          if (new_bind.key == default_bind.key && new_bind.modifier == default_bind.modifier) {
+            duplicate = true;
+            break;
+          }
+        }
+        if (!duplicate) {
+          keybinds.push_back(default_bind);
+        }
+      }
+      obj.keybinds = keybinds;
+    }
+  }
+  // if there is game specific configuration, override any values we just set
+  if (j.contains(version_to_game_name(obj.game_version))) {
+    from_json(j.at(version_to_game_name(obj.game_version)), obj);
+  }
+}
+
+std::string KeyBind::string() const {
+  switch (modifier) {
+    case KeyBind::Modifier::CTRL:
+      return fmt::format("CTRL-{}", key);
+    case KeyBind::Modifier::SHIFT:
+      return fmt::format("SHIFT-{}", key);
+    case KeyBind::Modifier::META:
+      return fmt::format("META-{}", key);
+  }
+}
+
+void to_json(json& j, const KeyBind& obj) {
+  j = json{{"description", obj.description}, {"command", obj.command}, {"key", obj.key}};
+  switch (obj.modifier) {
+    case KeyBind::Modifier::CTRL:
+      j["modifier"] = "ctrl";
+      break;
+    case KeyBind::Modifier::SHIFT:
+      j["modifier"] = "shift";
+      break;
+    case KeyBind::Modifier::META:
+      j["modifier"] = "meta";
+      break;
+  }
+}
+
+void from_json(const json& j, KeyBind& obj) {
+  j.at("description").get_to(obj.description);
+  j.at("command").get_to(obj.command);
+  j.at("key").get_to(obj.key);
+  auto modString = j.at("modifier").get<std::string>();
+  if (modString == "ctrl") {
+    obj.modifier = KeyBind::Modifier::CTRL;
+  } else if (modString == "shift") {
+    obj.modifier = KeyBind::Modifier::SHIFT;
+  } else if (modString == "meta") {
+    obj.modifier = KeyBind::Modifier::META;
+  }
+}
+}  // namespace REPL
diff --git a/common/repl/config.h b/common/repl/config.h
new file mode 100644
index 0000000000..c051ea5153
--- /dev/null
+++ b/common/repl/config.h
@@ -0,0 +1,50 @@
+#pragma once
+
+#include <optional>
+#include <string>
+#include <unordered_map>
+#include <vector>
+
+#include "common/versions.h"
+
+#include "third-party/json.hpp"
+
+using json = nlohmann::json;
+
+namespace REPL {
+struct KeyBind {
+  // NOTE - in my experience, meta doesn't work on windows and shift is probably a bad idea when
+  // typing text! but I leave it up to the user.
+  enum class Modifier { CTRL, SHIFT, META };
+  Modifier modifier;
+  std::string key;
+  std::string description;
+  std::string command;
+
+  std::string string() const;
+};
+void to_json(json& j, const KeyBind& obj);
+void from_json(const json& j, KeyBind& obj);
+
+struct Config {
+  GameVersion game_version;
+  Config(GameVersion _game_version) : game_version(_game_version){};
+
+  // this is the default REPL configuration
+  int target_connect_attempts = 30;
+  std::vector<std::string> asm_file_search_dirs = {};
+  bool append_keybinds = true;
+  std::vector<KeyBind> keybinds = {
+      {KeyBind::Modifier::CTRL, "T", "Starts up the game runtime", "(test-play)"},
+      {KeyBind::Modifier::CTRL, "Q", "Exit the REPL", "(e)"},
+      {KeyBind::Modifier::CTRL, "L", "Listen to an available game process", "(lt)"},
+      {KeyBind::Modifier::CTRL, "W",
+       "Halt the attached process so you can re-launch a crashed game", "(:stop)"},
+      {KeyBind::Modifier::CTRL, "G", "Attach the debugger to the process", "(dbgc)"},
+      {KeyBind::Modifier::CTRL, "B", "Displays the most recently caught backtrace", "(:di)"},
+      {KeyBind::Modifier::CTRL, "N", "Full build of the game", "(mi)"}};
+};
+void to_json(json& j, const Config& obj);
+void from_json(const json& j, Config& obj);
+
+}  // namespace REPL
diff --git a/common/nrepl/ReplClient.cpp b/common/repl/nrepl/ReplClient.cpp
similarity index 100%
rename from common/nrepl/ReplClient.cpp
rename to common/repl/nrepl/ReplClient.cpp
diff --git a/common/nrepl/ReplClient.h b/common/repl/nrepl/ReplClient.h
similarity index 100%
rename from common/nrepl/ReplClient.h
rename to common/repl/nrepl/ReplClient.h
diff --git a/common/nrepl/ReplServer.cpp b/common/repl/nrepl/ReplServer.cpp
similarity index 97%
rename from common/nrepl/ReplServer.cpp
rename to common/repl/nrepl/ReplServer.cpp
index c274bf694a..2286a8b8fd 100644
--- a/common/nrepl/ReplServer.cpp
+++ b/common/repl/nrepl/ReplServer.cpp
@@ -107,8 +107,8 @@ std::optional<std::string> ReplServer::get_msg() {
       auto req_bytes = read_from_socket(sock, header_buffer.data(), header_buffer.size());
       if (req_bytes == 0) {
         // Socket disconnected
-        // TODO - add a queue of messages in the ReplWrapper so we can print _BEFORE_ the prompt is
-        // output
+        // TODO - add a queue of messages in the REPL::Wrapper so we can print _BEFORE_ the prompt
+        // is output
         fmt::print("[nREPL:{}] Client Disconnected: {}\n", tcp_port, inet_ntoa(addr.sin_addr),
                    ntohs(addr.sin_port), sock);
 
diff --git a/common/nrepl/ReplServer.h b/common/repl/nrepl/ReplServer.h
similarity index 100%
rename from common/nrepl/ReplServer.h
rename to common/repl/nrepl/ReplServer.h
diff --git a/common/goos/ReplUtils.cpp b/common/repl/util.cpp
similarity index 52%
rename from common/goos/ReplUtils.cpp
rename to common/repl/util.cpp
index 62cedf0978..9fc926bba4 100644
--- a/common/goos/ReplUtils.cpp
+++ b/common/repl/util.cpp
@@ -1,22 +1,22 @@
-#include "ReplUtils.h"
+#include "util.h"
 
 #include "common/util/FileUtil.h"
+#include "common/util/json_util.h"
+#include "common/util/string_util.h"
 #include "common/versions.h"
 
 #include "third-party/fmt/color.h"
 #include "third-party/fmt/core.h"
 #include "third-party/replxx/include/replxx.hxx"
-
 // TODO - expand a list of hints (ie. a hint for defun to show at a glance how to write a function,
 // or perhaps, show the docstring for the current function being used?)
 
-using Replxx = replxx::Replxx;
-
-void ReplWrapper::clear_screen() {
+namespace REPL {
+void Wrapper::clear_screen() {
   repl.clear_screen();
 }
 
-void ReplWrapper::print_welcome_message() {
+void Wrapper::print_welcome_message() {
   // TODO - dont print on std-out
   // Welcome message / brief intro for documentation
   std::string ascii;
@@ -29,9 +29,9 @@ void ReplWrapper::print_welcome_message() {
 
   fmt::print("Welcome to OpenGOAL {}.{}!\n", versions::GOAL_VERSION_MAJOR,
              versions::GOAL_VERSION_MINOR);
-  fmt::print("Run ");
-  fmt::print(fmt::emphasis::bold | fg(fmt::color::cyan), "(repl-help)");
-  fmt::print(" for help with common commands and REPL usage.\n");
+  fmt::print("Run {} or {} for help with common commands and REPL usage.\n",
+             fmt::styled("(repl-help)", fmt::emphasis::bold | fg(fmt::color::cyan)),
+             fmt::styled("(repl-keybinds)", fmt::emphasis::bold | fg(fmt::color::cyan)));
   fmt::print("Run ");
   fmt::print(fmt::emphasis::bold | fg(fmt::color::cyan), "(lt)");
   fmt::print(" to connect to the local target.\n");
@@ -40,29 +40,29 @@ void ReplWrapper::print_welcome_message() {
   fmt::print(" to rebuild the entire game.\n\n");
 }
 
-void ReplWrapper::print_to_repl(const std::string_view& str) {
+void Wrapper::print_to_repl(const std::string& str) {
   repl.print(str.data());
 }
 
-void ReplWrapper::set_history_max_size(size_t len) {
+void Wrapper::set_history_max_size(size_t len) {
   repl.set_max_history_size(len);
 }
 
-const char* ReplWrapper::readline(const std::string& prompt) {
+const char* Wrapper::readline(const std::string& prompt) {
   return repl.input(prompt);
 }
 
-void ReplWrapper::add_to_history(const std::string& line) {
+void Wrapper::add_to_history(const std::string& line) {
   repl.history_add(line);
 }
 
-void ReplWrapper::save_history() {
+void Wrapper::save_history() {
   fs::path path = file_util::get_user_config_dir() / ".opengoal.repl.history";
   file_util::create_dir_if_needed_for_file(path.string());
   repl.history_save(path.string());
 }
 
-void ReplWrapper::load_history() {
+void Wrapper::load_history() {
   fs::path path = file_util::get_user_config_dir() / ".opengoal.repl.history";
   if (fs::exists(path)) {
     repl.history_load(path.string());
@@ -71,7 +71,7 @@ void ReplWrapper::load_history() {
   }
 }
 
-std::pair<std::string, bool> ReplWrapper::get_current_repl_token(std::string const& context) {
+std::pair<std::string, bool> Wrapper::get_current_repl_token(std::string const& context) {
   // Find the current token
   std::string token = "";
   for (auto c = context.crbegin(); c != context.crend(); c++) {
@@ -90,7 +90,7 @@ std::pair<std::string, bool> ReplWrapper::get_current_repl_token(std::string con
   return {token, false};
 }
 
-void ReplWrapper::print_help_message() {
+void Wrapper::print_help_message() {
   fmt::print(fmt::emphasis::bold, "\nREPL Controls:\n");
   fmt::print(fmt::emphasis::bold | fg(fmt::color::cyan), "(:clear)\n");
   fmt::print(" - Clear the current screen\n");
@@ -130,31 +130,110 @@ void ReplWrapper::print_help_message() {
   fmt::print(" - Enter a GOOS REPL\n");
 }
 
-replxx::Replxx::key_press_handler_t ReplWrapper::commit_text_action(std::string text_to_commit) {
+void Wrapper::print_keybind_help() {
+  fmt::print(fmt::emphasis::bold, "\nREPL KeyBinds:\n");
+  for (const auto& bind : repl_config.keybinds) {
+    fmt::print("{}\n", fmt::styled(bind.string(), fmt::fg(fmt::color::cyan)));
+    fmt::print("{}\n", fmt::styled(bind.description, fmt::fg(fmt::color::gray)));
+  }
+}
+
+replxx::Replxx::key_press_handler_t Wrapper::commit_text_action(std::string text_to_commit) {
   return [this, text_to_commit](char32_t code) {
     repl.set_state(
         replxx::Replxx::State(text_to_commit.c_str(), static_cast<int>(text_to_commit.size())));
-    return repl.invoke(Replxx::ACTION::COMMIT_LINE, code);
+    return repl.invoke(replxx::Replxx::ACTION::COMMIT_LINE, code);
   };
 }
 
-void ReplWrapper::init_default_settings() {
+void Wrapper::init_settings() {
   // NOTE - a nice popular project that uses replxx
   // - https://github.com/ClickHouse/ClickHouse/blob/master/base/base/ReplxxLineReader.cpp#L366
   repl.set_word_break_characters(" \t");
   // Setup default keybinds
-  // (test-play) : Ctrl-T
-  repl.bind_key(Replxx::KEY::control('T'), commit_text_action("(test-play)"));
-  // (e) : Ctrl-Q
-  repl.bind_key(Replxx::KEY::control('Q'), commit_text_action("(e)"));
-  // (lt) : Ctrl-L
-  repl.bind_key(Replxx::KEY::control('L'), commit_text_action("(lt)"));
-  /// (:stop) : Ctrl-W
-  repl.bind_key(Replxx::KEY::control('W'), commit_text_action("(:stop)"));
-  // (dbgc) : Ctrl-G
-  repl.bind_key(Replxx::KEY::control('G'), commit_text_action("(dbgc)"));
-  // (:di) : Ctrl-B
-  repl.bind_key(Replxx::KEY::control('B'), commit_text_action("(:di)"));
-  // (mi) : Ctrl-N
-  repl.bind_key(Replxx::KEY::control('N'), commit_text_action("(mi)"));
+  for (const auto& bind : repl_config.keybinds) {
+    char32_t code;
+    switch (bind.modifier) {
+      case KeyBind::Modifier::CTRL:
+        code = replxx::Replxx::KEY::control(bind.key.at(0));
+        break;
+      case KeyBind::Modifier::SHIFT:
+        code = replxx::Replxx::KEY::shift(bind.key.at(0));
+        break;
+      case KeyBind::Modifier::META:
+        code = replxx::Replxx::KEY::meta(bind.key.at(0));
+        break;
+    }
+    repl.bind_key(code, commit_text_action(bind.command));
+  }
 }
+
+// TODO - command to print out keybinds
+
+void Wrapper::reload_startup_file() {
+  startup_file = load_user_startup_file(username);
+}
+
+std::string find_repl_username() {
+  // Two options - either:
+  // 1. look for the `user.txt` file, which should only contain the username
+  // 2. if this is absent AND there is a single folder inside the "user" folder, use that as the
+  // username
+  auto user_dir = file_util::get_jak_project_dir() / "goal_src" / "user";
+  auto dirs = file_util::find_directories_in_dir(user_dir);
+  if (dirs.size() == 1) {
+    return dirs.at(0).filename().string();
+  }
+
+  std::regex allowed_chars("(^[0-9a-zA-Z\\-\\.\\!\\?<>]*$)");
+  if (file_util::file_exists((user_dir / "user.txt").string())) {
+    auto text = file_util::read_text_file(user_dir / "user.txt");
+    text = str_util::trim(text);
+    if (!text.empty() && std::regex_match(text, allowed_chars)) {
+      return text;
+    }
+  }
+
+  return "#f";
+}
+
+StartupFile load_user_startup_file(const std::string& username) {
+  // Check for a `startup.gc` file, each line will be executed on the REPL on startup
+  auto startup_file_path =
+      file_util::get_jak_project_dir() / "goal_src" / "user" / username / "startup.gc";
+  StartupFile startup_file;
+  if (file_util::file_exists(startup_file_path.string())) {
+    auto data = file_util::read_text_file(startup_file_path);
+    auto startup_cmds = str_util::split(data);
+    bool found_run_on_listen_line = false;
+    for (const auto& cmd : startup_cmds) {
+      if (found_run_on_listen_line) {
+        startup_file.run_after_listen.push_back(cmd);
+      } else {
+        startup_file.run_before_listen.push_back(cmd);
+      }
+      if (str_util::contains(cmd, "og:run-below-on-listen")) {
+        found_run_on_listen_line = true;
+      }
+    }
+  }
+  return startup_file;
+}
+
+REPL::Config load_repl_config(const std::string& username, const GameVersion game_version) {
+  auto repl_config_path =
+      file_util::get_jak_project_dir() / "goal_src" / "user" / username / "repl-config.json";
+  if (file_util::file_exists(repl_config_path.string())) {
+    try {
+      REPL::Config config(game_version);
+      auto repl_config_data =
+          parse_commented_json(file_util::read_text_file(repl_config_path), "repl-config.json");
+      from_json(repl_config_data, config);
+      return config;
+    } catch (std::exception& e) {
+      REPL::Config config(game_version);
+    }
+  }
+  return REPL::Config(game_version);
+}
+}  // namespace REPL
diff --git a/common/repl/util.h b/common/repl/util.h
new file mode 100644
index 0000000000..d12b0c573f
--- /dev/null
+++ b/common/repl/util.h
@@ -0,0 +1,56 @@
+#pragma once
+
+#include <functional>
+#include <optional>
+#include <string>
+#include <vector>
+
+#include "config.h"
+
+#include "third-party/replxx/include/replxx.hxx"
+
+namespace REPL {
+
+struct StartupFile {
+  std::vector<std::string> run_before_listen = {};
+  std::vector<std::string> run_after_listen = {};
+};
+
+class Wrapper {
+  replxx::Replxx repl;
+
+ public:
+  std::string username;
+  Config repl_config;
+  StartupFile startup_file;
+  std::vector<std::string> examples{};
+  std::vector<std::pair<std::string, replxx::Replxx::Color>> regex_colors{};
+
+  Wrapper(const std::string& _username, const Config& config, const StartupFile& startup)
+      : username(_username), repl_config(config), startup_file(startup) {}
+  replxx::Replxx& get_repl() { return repl; }
+  void init_settings();
+  void reload_startup_file();
+
+  // Functionality / Commands
+  void clear_screen();
+  void print_to_repl(const std::string& str);
+  void print_welcome_message();
+  void set_history_max_size(size_t len);
+  const char* readline(const std::string& prompt);
+  void add_to_history(const std::string& line);
+  void save_history();
+  void load_history();
+  void print_help_message();
+  void print_keybind_help();
+  std::pair<std::string, bool> get_current_repl_token(std::string const& context);
+
+ private:
+  replxx::Replxx::key_press_handler_t commit_text_action(std::string text_to_commit);
+  std::vector<REPL::KeyBind> keybindings = {};
+};
+
+std::string find_repl_username();
+StartupFile load_user_startup_file(const std::string& username);
+REPL::Config load_repl_config(const std::string& username, const GameVersion game_version);
+}  // namespace REPL
diff --git a/common/util/FileUtil.cpp b/common/util/FileUtil.cpp
index eb1dabbfb6..8e9de81640 100644
--- a/common/util/FileUtil.cpp
+++ b/common/util/FileUtil.cpp
@@ -550,4 +550,14 @@ std::vector<fs::path> find_files_recursively(const fs::path& base_dir, const std
   return files;
 }
 
+std::vector<fs::path> find_directories_in_dir(const fs::path& base_dir) {
+  std::vector<fs::path> dirs = {};
+  for (auto& p : fs::recursive_directory_iterator(base_dir)) {
+    if (p.is_directory()) {
+      dirs.push_back(p.path());
+    }
+  }
+  return dirs;
+}
+
 }  // namespace file_util
diff --git a/common/util/FileUtil.h b/common/util/FileUtil.h
index 10c6869f42..49de36971b 100644
--- a/common/util/FileUtil.h
+++ b/common/util/FileUtil.h
@@ -60,4 +60,5 @@ bool dgo_header_is_compressed(const std::vector<u8>& data);
 std::vector<u8> decompress_dgo(const std::vector<u8>& data_in);
 FILE* open_file(const fs::path& path, const std::string& mode);
 std::vector<fs::path> find_files_recursively(const fs::path& base_dir, const std::regex& pattern);
+std::vector<fs::path> find_directories_in_dir(const fs::path& base_dir);
 }  // namespace file_util
diff --git a/common/util/diff.cpp b/common/util/diff.cpp
index 7b6890e80c..0e61b8eb78 100644
--- a/common/util/diff.cpp
+++ b/common/util/diff.cpp
@@ -296,6 +296,8 @@ std::vector<std::string> SplitString(const ::std::string& str, char delimiter =
 }
 
 }  // namespace
+
+namespace google_diff {
 std::string diff_strings(const std::string& lhs, const std::string& rhs) {
   if (!lhs.empty() && !rhs.empty()) {
     const std::vector<std::string> lhs_lines = SplitString(lhs);
@@ -310,3 +312,4 @@ std::string diff_strings(const std::string& lhs, const std::string& rhs) {
 std::vector<std::string> split_string(const ::std::string& str, char delimiter) {
   return SplitString(str, delimiter);
 }
+}  // namespace google_diff
diff --git a/common/util/diff.h b/common/util/diff.h
index 8dac5a4875..3eab1d5374 100644
--- a/common/util/diff.h
+++ b/common/util/diff.h
@@ -6,6 +6,7 @@
 /*!
  * Diff two strings. This uses the code from gtest's diff implementation.
  */
+namespace google_diff {
 std::string diff_strings(const std::string& lhs, const std::string& rhs);
-
 std::vector<std::string> split_string(const ::std::string& str, char delimiter = '\n');
+}  // namespace google_diff
diff --git a/common/util/string_util.cpp b/common/util/string_util.cpp
index cefb956643..44b89a4cce 100644
--- a/common/util/string_util.cpp
+++ b/common/util/string_util.cpp
@@ -2,6 +2,8 @@
 
 #include <regex>
 
+#include "common/util/diff.h"
+
 namespace str_util {
 
 const std::string WHITESPACE = " \n\r\t\f\v";
@@ -47,4 +49,12 @@ bool valid_regex(const std::string& regex) {
   }
   return true;
 }
+
+std::string diff(const std::string& lhs, const std::string& rhs) {
+  return google_diff::diff_strings(lhs, rhs);
+}
+/// Default splits on \n characters
+std::vector<std::string> split(const ::std::string& str, char delimiter) {
+  return google_diff::split_string(str, delimiter);
+}
 }  // namespace str_util
diff --git a/common/util/string_util.h b/common/util/string_util.h
index 3e6b8f9209..e93054d897 100644
--- a/common/util/string_util.h
+++ b/common/util/string_util.h
@@ -1,4 +1,7 @@
+#pragma once
+
 #include <string>
+#include <vector>
 
 namespace str_util {
 bool contains(const std::string& s, const std::string& substr);
@@ -8,4 +11,7 @@ std::string rtrim(const std::string& s);
 std::string trim(const std::string& s);
 int line_count(const std::string& str);
 bool valid_regex(const std::string& regex);
+std::string diff(const std::string& lhs, const std::string& rhs);
+/// Default splits on \n characters
+std::vector<std::string> split(const ::std::string& str, char delimiter = '\n');
 }  // namespace str_util
diff --git a/common/versions.cpp b/common/versions.cpp
index 945ce15453..72932c04d7 100644
--- a/common/versions.cpp
+++ b/common/versions.cpp
@@ -29,3 +29,7 @@ std::string version_to_game_name(GameVersion v) {
       ASSERT_MSG(false, fmt::format("no game_name for version: {} found", fmt::underlying(v)));
   }
 }
+
+std::vector<std::string> valid_game_version_names() {
+  return {game_version_names[GameVersion::Jak1], game_version_names[GameVersion::Jak2]};
+}
diff --git a/common/versions.h b/common/versions.h
index f3d41089f3..e5904f6971 100644
--- a/common/versions.h
+++ b/common/versions.h
@@ -6,6 +6,7 @@
  */
 
 #include <string>
+#include <vector>
 
 #include "common/common_types.h"
 
@@ -55,3 +56,4 @@ constexpr PerGameVersion<const char*> game_version_names = {"jak1", "jak2"};
 GameVersion game_name_to_version(const std::string& name);
 bool valid_game_version(const std::string& name);
 std::string version_to_game_name(GameVersion v);
+std::vector<std::string> valid_game_version_names();
diff --git a/game/tools/subtitles/subtitle_editor.h b/game/tools/subtitles/subtitle_editor.h
index f07a826ea3..655e16355d 100644
--- a/game/tools/subtitles/subtitle_editor.h
+++ b/game/tools/subtitles/subtitle_editor.h
@@ -3,7 +3,7 @@
 #include <optional>
 #include <string_view>
 
-#include "common/nrepl/ReplClient.h"
+#include "common/repl/nrepl/ReplClient.h"
 #include "common/serialization/subtitles/subtitles_ser.h"
 
 #include "third-party/imgui/imgui.h"
diff --git a/goal_src/user/readme.md b/goal_src/user/readme.md
index cbd2c419d0..d4f5d66f53 100644
--- a/goal_src/user/readme.md
+++ b/goal_src/user/readme.md
@@ -5,6 +5,8 @@ e.g. for username `mark` make a directory called `mark`
 Inside that directory, create `user.gs` and `user.gc` files.
 These are your own user scripts, loaded after the GOOS library and GOAL library respectively.
 
+> Alternatively, if you only have a single folder in `goal_src/user/` it will be assumed to be your user folder
+
 The rest of the directory can be used however you please!
 
 To automatically log in as a specific user, create a `user.txt` file in this directory
@@ -13,7 +15,60 @@ modify multiple scripts when you want to change users.
 
 If you want to make your profile public, edit the .gitignore in this directory.
 
-Additionally, you can provide a `repl-config.json` to set various REPL settings:
-- `numConnectToTargetAttempts` - the number of times the REPL will attempt to connect to the target on an `(lt)`
+Additionally, you can provide a `repl-config.json` to set various REPL settings, an example configuration:
+```json
+{
+  "numConnectToTargetAttempts": 1,
+  "jak1": {
+    "asmFileSearchDirs": [
+      "goal_src/jak1"
+    ]
+  },
+  "jak2": {
+    "asmFileSearchDirs": [
+      "goal_src/jak2"
+    ]
+  },
+  "appendKeybinds": true,
+  "keybinds": [
+    {
+      "modifier": "ctrl",
+      "key": "S",
+      "description": "Test Bind",
+      "command": "(format 0 \"hello world\")"
+    }
+  ]
+}
+```
 
 And a `startup.gc` where each line will be executed upon startup
+
+## Re-running certain commands upon listening to the target
+
+A common workflow that you might want in your `startup.gc` is something like the following:
+
+```clj
+(mi)
+(lt)
+(dbgc)
+(test-play)
+```
+
+This builds the game, connects to the game, attaches the debugger, and runs it.
+
+However, when you crash you ideally want to just be able to:
+- stop the game via `(:stop)` or the respective keybind
+- fix the code, rebuild just that file
+- re-launch the game and re-connect
+
+Upon which you'd probably want to run all or some of the above startup again.  But how can you accomplish this without re-launching the REPL completely?  Like so:
+
+```clj
+(mi)
+(lt)
+;; og:run-below-on-listen
+(dbgc)
+(test-play)
+```
+
+As the comment suggests, upon a succesful `(lt)` it will run any lines below it again.
diff --git a/goalc/compiler/Compiler.cpp b/goalc/compiler/Compiler.cpp
index 46088fc995..7a6e29263b 100644
--- a/goalc/compiler/Compiler.cpp
+++ b/goalc/compiler/Compiler.cpp
@@ -20,7 +20,7 @@ using namespace goos;
 
 Compiler::Compiler(GameVersion version,
                    const std::string& user_profile,
-                   std::unique_ptr<ReplWrapper> repl)
+                   std::unique_ptr<REPL::Wrapper> repl)
     : m_version(version),
       m_goos(user_profile),
       m_debugger(&m_listener, &m_goos.reader, version),
@@ -63,9 +63,9 @@ Compiler::Compiler(GameVersion version,
     m_repl->load_history();
     // init repl
     m_repl->print_welcome_message();
-    auto examples = m_repl->examples;
-    auto regex_colors = m_repl->regex_colors;
-    m_repl->init_default_settings();
+    auto& examples = m_repl->examples;
+    auto& regex_colors = m_repl->regex_colors;
+    m_repl->init_settings();
     using namespace std::placeholders;
     m_repl->get_repl().set_completion_callback(std::bind(
         &Compiler::find_symbols_or_object_file_by_prefix, this, _1, _2, std::cref(examples)));
@@ -397,7 +397,7 @@ void Compiler::asm_file(const CompilationOptions& options) {
     if (file_path.empty()) {
       lg::print("ERROR - can't load a file without a providing a path\n");
       return;
-    } else if (m_asm_file_search_dirs.empty()) {
+    } else if (m_repl && m_repl->repl_config.asm_file_search_dirs.empty()) {
       lg::print(
           "ERROR - can't load a file that doesn't exist - '{}' and no search dirs are defined\n",
           file_path);
@@ -406,14 +406,17 @@ void Compiler::asm_file(const CompilationOptions& options) {
     std::string base_name = file_util::base_name_no_ext(file_path);
     // Attempt the find the full path of the file (ignore extension)
     std::vector<fs::path> candidate_paths = {};
-    for (const auto& dir : m_asm_file_search_dirs) {
-      std::string base_dir = file_util::get_file_path({dir});
-      const auto& results = file_util::find_files_recursively(
-          base_dir, std::regex(fmt::format("^{}(\\..*)?$", base_name)));
-      for (const auto& result : results) {
-        candidate_paths.push_back(result);
+    if (m_repl) {
+      for (const auto& dir : m_repl->repl_config.asm_file_search_dirs) {
+        std::string base_dir = file_util::get_file_path({dir});
+        const auto& results = file_util::find_files_recursively(
+            base_dir, std::regex(fmt::format("^{}(\\..*)?$", base_name)));
+        for (const auto& result : results) {
+          candidate_paths.push_back(result);
+        }
       }
     }
+
     if (candidate_paths.empty()) {
       lg::print("ERROR - attempt to find object file automatically, but found nothing\n");
       return;
diff --git a/goalc/compiler/Compiler.h b/goalc/compiler/Compiler.h
index bd41b63364..351b62818f 100644
--- a/goalc/compiler/Compiler.h
+++ b/goalc/compiler/Compiler.h
@@ -5,7 +5,7 @@
 #include <optional>
 
 #include "common/goos/Interpreter.h"
-#include "common/goos/ReplUtils.h"
+#include "common/repl/util.h"
 #include "common/type_system/TypeSystem.h"
 
 #include "goalc/compiler/CompilerException.h"
@@ -41,12 +41,12 @@ class Compiler {
  public:
   Compiler(GameVersion version,
            const std::string& user_profile = "#f",
-           std::unique_ptr<ReplWrapper> repl = nullptr);
+           std::unique_ptr<REPL::Wrapper> repl = nullptr);
   ~Compiler();
   void asm_file(const CompilationOptions& options);
 
   void save_repl_history();
-  void print_to_repl(const std::string_view& str);
+  void print_to_repl(const std::string& str);
   std::string get_prompt();
   std::string get_repl_input();
   ReplStatus handle_repl_string(const std::string& input);
@@ -81,21 +81,19 @@ class Compiler {
   listener::Listener& listener() { return m_listener; }
   void poke_target() { m_listener.send_poke(); }
   bool connect_to_target();
-  Replxx::completions_t find_symbols_or_object_file_by_prefix(
+  replxx::Replxx::completions_t find_symbols_or_object_file_by_prefix(
       std::string const& context,
       int& contextLen,
       std::vector<std::string> const& user_data);
-  Replxx::hints_t find_hints_by_prefix(std::string const& context,
-                                       int& contextLen,
-                                       Replxx::Color& color,
-                                       std::vector<std::string> const& user_data);
+  replxx::Replxx::hints_t find_hints_by_prefix(std::string const& context,
+                                               int& contextLen,
+                                               replxx::Replxx::Color& color,
+                                               std::vector<std::string> const& user_data);
   void repl_coloring(std::string const& str,
-                     Replxx::colors_t& colors,
-                     std::vector<std::pair<std::string, Replxx::Color>> const& user_data);
+                     replxx::Replxx::colors_t& colors,
+                     std::vector<std::pair<std::string, replxx::Replxx::Color>> const& user_data);
   bool knows_object_file(const std::string& name);
   MakeSystem& make_system() { return m_make; }
-  void update_via_config_file(const std::string& json,
-                              const std::optional<std::string> game_name = {});
 
  private:
   GameVersion m_version;
@@ -114,13 +112,9 @@ class Compiler {
   bool m_throw_on_define_extern_redefinition = false;
   std::unordered_set<std::string> m_allow_inconsistent_definition_symbols;
   SymbolInfoMap m_symbol_info;
-  std::unique_ptr<ReplWrapper> m_repl;
+  std::unique_ptr<REPL::Wrapper> m_repl;
   MakeSystem m_make;
 
-  // Configurable fields
-  int m_target_connect_attempts = 30;
-  std::vector<std::string> m_asm_file_search_dirs = {};
-
   struct DebugStats {
     int num_spills = 0;
     int num_spills_v1 = 0;
@@ -602,6 +596,7 @@ class Compiler {
   Val* compile_asm_data_file(const goos::Object& form, const goos::Object& rest, Env* env);
   Val* compile_asm_text_file(const goos::Object& form, const goos::Object& rest, Env* env);
   Val* compile_repl_help(const goos::Object& form, const goos::Object& rest, Env* env);
+  Val* compile_repl_keybinds(const goos::Object& form, const goos::Object& rest, Env* env);
   Val* compile_listen_to_target(const goos::Object& form, const goos::Object& rest, Env* env);
   Val* compile_reset_target(const goos::Object& form, const goos::Object& rest, Env* env);
   Val* compile_poke(const goos::Object& form, const goos::Object& rest, Env* env);
diff --git a/goalc/compiler/Util.cpp b/goalc/compiler/Util.cpp
index c0cb4536de..a1a4e12d09 100644
--- a/goalc/compiler/Util.cpp
+++ b/goalc/compiler/Util.cpp
@@ -9,7 +9,7 @@ void Compiler::save_repl_history() {
   m_repl->save_history();
 }
 
-void Compiler::print_to_repl(const std::string_view& str) {
+void Compiler::print_to_repl(const std::string& str) {
   m_repl->print_to_repl(str);
 }
 
@@ -154,22 +154,6 @@ bool Compiler::knows_object_file(const std::string& name) {
   return m_debugger.knows_object(name);
 }
 
-void Compiler::update_via_config_file(const std::string& json,
-                                      const std::optional<std::string> game_name) {
-  auto cfg = parse_commented_json(json, "repl-config.json");
-  if (cfg.contains("numConnectToTargetAttempts")) {
-    m_target_connect_attempts = cfg.at("numConnectToTargetAttempts").get<int>();
-  }
-  if (cfg.contains("asmFileSearchDirs")) {
-    m_asm_file_search_dirs = cfg.at("asmFileSearchDirs").get<std::vector<std::string>>();
-  }
-  // If there are any game specific config entries, set or override with them
-  if (game_name && cfg.contains(game_name.value())) {
-    auto game_cfg = cfg.at(game_name.value()).get<nlohmann::json>();
-    update_via_config_file(game_cfg.dump(), {});
-  }
-}
-
 /*!
  * Parse arguments into a goos::Arguments format.
  */
diff --git a/goalc/compiler/compilation/Atoms.cpp b/goalc/compiler/compilation/Atoms.cpp
index c928f883d3..2ff6bd9a71 100644
--- a/goalc/compiler/compilation/Atoms.cpp
+++ b/goalc/compiler/compilation/Atoms.cpp
@@ -140,6 +140,7 @@ const std::unordered_map<
 
         // COMPILER CONTROL
         {"repl-help", &Compiler::compile_repl_help},
+        {"repl-keybinds", &Compiler::compile_repl_keybinds},
         {":clear", &Compiler::compile_repl_clear_screen},
         {"gs", &Compiler::compile_gs},
         {":exit", &Compiler::compile_exit},
diff --git a/goalc/compiler/compilation/CompilerControl.cpp b/goalc/compiler/compilation/CompilerControl.cpp
index 6e853ea843..8b50bed433 100644
--- a/goalc/compiler/compilation/CompilerControl.cpp
+++ b/goalc/compiler/compilation/CompilerControl.cpp
@@ -6,7 +6,7 @@
 #include <regex>
 #include <stack>
 
-#include "common/goos/ReplUtils.h"
+#include "common/repl/util.h"
 #include "common/util/DgoWriter.h"
 #include "common/util/FileUtil.h"
 #include "common/util/Timer.h"
@@ -177,6 +177,14 @@ Val* Compiler::compile_repl_help(const goos::Object&, const goos::Object&, Env*)
   return get_none();
 }
 
+/*!
+ * Print out all set keybinds for the REPL (by our tooling)
+ */
+Val* Compiler::compile_repl_keybinds(const goos::Object&, const goos::Object&, Env*) {
+  m_repl.get()->print_keybind_help();
+  return get_none();
+}
+
 /*!
  * Connect the compiler to a target. Takes an optional IP address / port, defaults to
  * 127.0.0.1 and 8112, which is the local computer and the default port for the DECI2 over IP
@@ -208,7 +216,17 @@ Val* Compiler::compile_listen_to_target(const goos::Object& form,
     }
   });
 
-  m_listener.connect_to_target(m_target_connect_attempts, ip, port);
+  int retries = 30;
+  if (m_repl) {
+    retries = m_repl->repl_config.target_connect_attempts;
+  }
+  auto connected = m_listener.connect_to_target(retries, ip, port);
+  if (connected && m_repl) {
+    m_repl->reload_startup_file();
+    for (const auto& line : m_repl->startup_file.run_after_listen) {
+      handle_repl_string(line);
+    }
+  }
   return get_none();
 }
 
@@ -379,13 +397,13 @@ Val* Compiler::compile_get_info(const goos::Object& form, const goos::Object& re
   return get_none();
 }
 
-Replxx::completions_t Compiler::find_symbols_or_object_file_by_prefix(
+replxx::Replxx::completions_t Compiler::find_symbols_or_object_file_by_prefix(
     std::string const& context,
     int& contextLen,
     std::vector<std::string> const& user_data) {
   (void)contextLen;
   (void)user_data;
-  Replxx::completions_t completions;
+  replxx::Replxx::completions_t completions;
 
   // If we are trying to execute a `(ml ...)` we can automatically get the object file
   // insert quotes if needed as well.
@@ -418,16 +436,16 @@ Replxx::completions_t Compiler::find_symbols_or_object_file_by_prefix(
   return completions;
 }
 
-Replxx::hints_t Compiler::find_hints_by_prefix(std::string const& context,
-                                               int& contextLen,
-                                               Replxx::Color& color,
-                                               std::vector<std::string> const& user_data) {
+replxx::Replxx::hints_t Compiler::find_hints_by_prefix(std::string const& context,
+                                                       int& contextLen,
+                                                       replxx::Replxx::Color& color,
+                                                       std::vector<std::string> const& user_data) {
   (void)contextLen;
   (void)user_data;
   auto token = m_repl->get_current_repl_token(context);
   auto possible_forms = lookup_symbol_infos_starting_with(token.first);
 
-  Replxx::hints_t hints;
+  replxx::Replxx::hints_t hints;
 
   // TODO - hints for `(ml ...` as well
 
@@ -440,7 +458,7 @@ Replxx::hints_t Compiler::find_hints_by_prefix(std::string const& context,
 
   // set hint color to green if single match found
   if (hints.size() == 1) {
-    color = Replxx::Color::GREEN;
+    color = replxx::Replxx::Color::GREEN;
   }
 
   return hints;
@@ -448,10 +466,10 @@ Replxx::hints_t Compiler::find_hints_by_prefix(std::string const& context,
 
 void Compiler::repl_coloring(
     std::string const& context,
-    Replxx::colors_t& colors,
-    std::vector<std::pair<std::string, Replxx::Color>> const& regex_color) {
+    replxx::Replxx::colors_t& colors,
+    std::vector<std::pair<std::string, replxx::Replxx::Color>> const& regex_color) {
   (void)regex_color;
-  using cl = Replxx::Color;
+  using cl = replxx::Replxx::Color;
   // TODO - a proper circular queue would be cleaner to use
   std::deque<cl> paren_colors = {cl::GREEN, cl::CYAN, cl::MAGENTA};
   std::stack<std::pair<char, cl>> expression_stack;
diff --git a/goalc/main.cpp b/goalc/main.cpp
index 72c67e5792..91996157ad 100644
--- a/goalc/main.cpp
+++ b/goalc/main.cpp
@@ -1,11 +1,12 @@
 #include <cstdio>
 #include <regex>
 
-#include "common/goos/ReplUtils.h"
 #include "common/log/log.h"
-#include "common/nrepl/ReplServer.h"
+#include "common/repl/nrepl/ReplServer.h"
+#include "common/repl/util.h"
 #include "common/util/FileUtil.h"
 #include "common/util/diff.h"
+#include "common/util/string_util.h"
 #include "common/versions.h"
 
 #include "goalc/compiler/Compiler.h"
@@ -27,7 +28,6 @@ int main(int argc, char** argv) {
   bool auto_debug = false;
   bool auto_find_user = false;
   std::string cmd = "";
-  std::string startup_cmd = "";
   std::string username = "#f";
   std::string game = "jak1";
   int nrepl_port = 8181;
@@ -36,9 +36,7 @@ int main(int argc, char** argv) {
   // TODO - a lot of these flags could be deprecated and moved into `repl-config.json`
   // TODO - auto-find the user if there is only one folder within `user/`
   CLI::App app{"OpenGOAL Compiler / REPL"};
-  app.add_option("-c,--cmd", cmd, "Specify a command to run");
-  app.add_option("--startup-cmd", startup_cmd,
-                 "Specify a command to run and keep the REPL open afterwards");
+  app.add_option("-c,--cmd", cmd, "Specify a command to run, no REPL is launched in this mode");
   app.add_option("-u,--user", username,
                  "Specify the username to use for your user profile in 'goal_src/user/'");
   app.add_option("-p,--port", nrepl_port, "Specify the nREPL port.  Defaults to 8181");
@@ -47,13 +45,25 @@ int main(int argc, char** argv) {
   app.add_flag("--auto-dbg", auto_debug,
                "Attempt to automatically connect to the debugger on startup");
   app.add_flag("--user-auto", auto_find_user,
-               "Attempt to automatically deduce the user, overrides '-user'");
+               "Attempt to automatically deduce the user, overrides '--user'");
   app.add_option("-g,--game", game, "The game name: 'jak1' or 'jak2'");
   app.add_option("--proj-path", project_path_override,
                  "Specify the location of the 'data/' folder");
   app.validate_positionals();
   CLI11_PARSE(app, argc, argv);
 
+  // Yell about deprecations
+  if (auto_listen) {
+    lg::warn(
+        "--auto-lt will be deprecated, migrate to a 'startup.gc' file in your goal_src/user "
+        "folder");
+  }
+  if (auto_debug) {
+    lg::warn(
+        "--auto-dbg will be deprecated, migrate to a 'startup.gc' file in your goal_src/user "
+        "folder");
+  }
+
   GameVersion game_version = game_name_to_version(game);
 
   if (!project_path_override.empty()) {
@@ -69,74 +79,60 @@ int main(int argc, char** argv) {
     return 1;
   }
 
-  std::vector<std::string> user_startup_commands = {};
-  std::optional<std::string> repl_config = {};
-
-  if (auto_find_user) {
-    username = "#f";
-    std::regex allowed_chars("[0-9a-zA-Z\\-\\.\\!\\?<>]");
-    try {
-      auto text = std::make_shared<goos::FileText>(
-          file_util::get_file_path({"goal_src", "user", "user.txt"}), "goal_src/user/user.txt");
-      goos::TextStream ts(text);
-      ts.seek_past_whitespace_and_comments();
-      std::string found_username;
-      while (ts.text_remains()) {
-        auto character = ts.read();
-        if (!std::regex_match(std::string(1, character), allowed_chars)) {
-          break;
-        }
-        found_username.push_back(character);
-      }
-      if (!found_username.empty()) {
-        username = found_username;
-        // Check for a `startup.gc` file, each line will be executed on the REPL on startup
-        auto startup_file_path =
-            file_util::get_file_path({"goal_src", "user", username, "startup.gc"});
-        if (file_util::file_exists(startup_file_path)) {
-          auto data = file_util::read_text_file(startup_file_path);
-          auto startup_cmds = split_string(data);
-          for (const auto& cmd : startup_cmds) {
-            user_startup_commands.push_back(cmd);
-          }
-        }
-        // Check for a `repl-config.json` file, so things can be configured without tons of flags
-        auto repl_config_path =
-            file_util::get_file_path({"goal_src", "user", username, "repl-config.json"});
-        if (file_util::file_exists(repl_config_path)) {
-          repl_config = file_util::read_text_file(repl_config_path);
-        }
-      }
-    } catch (std::exception& e) {
-      printf("error opening user desc file: %s\n", e.what());
-    }
-  }
-
   setup_logging();
-
   lg::info("OpenGOAL Compiler {}.{}", versions::GOAL_VERSION_MAJOR, versions::GOAL_VERSION_MINOR);
 
-  // Init REPL
+  // Figure out the username
+  if (auto_find_user) {
+    username = REPL::find_repl_username();
+  }
+  // Load the user's startup file
+  auto startup_file = REPL::load_user_startup_file(username);
+  // TODO - deprecate these two flags
+  if (startup_file.run_before_listen.empty() && (auto_debug || auto_listen)) {
+    startup_file.run_before_listen.push_back("(lt)");
+  }
+  if (startup_file.run_after_listen.empty() && (auto_debug || auto_listen)) {
+    startup_file.run_before_listen.push_back("(dbgc)");
+  }
+  // Load the user's REPL config
+  auto repl_config = REPL::load_repl_config(username, game_version);
+
+  // Init Compiler
+  std::unique_ptr<Compiler> compiler;
+  std::mutex compiler_mutex;
+  // if a command is provided on the command line, no REPL just run the compiler on it
+  try {
+    if (!cmd.empty()) {
+      compiler = std::make_unique<Compiler>(game_version);
+      compiler->run_front_end_on_string(cmd);
+      return 0;
+    }
+  } catch (std::exception& e) {
+    lg::error("Compiler Fatal Error: {}", e.what());
+  }
+
+  // Otherwise, start the REPL normally
   ReplStatus status = ReplStatus::OK;
+  std::function<void()> repl_startup_func = [&]() {
+    // Run automatic forms if applicable
+    std::lock_guard<std::mutex> lock(compiler_mutex);
+    for (const auto& cmd : startup_file.run_before_listen) {
+      status = compiler->handle_repl_string(cmd);
+    }
+  };
+
+  // Initialize nREPL server socket
   std::function<bool()> shutdown_callback = [&]() { return status == ReplStatus::WANT_EXIT; };
   ReplServer repl_server(shutdown_callback, nrepl_port);
   bool repl_server_ok = repl_server.init_server();
   std::thread nrepl_thread;
   // the compiler may throw an exception if it fails to load its standard library.
   try {
-    std::unique_ptr<Compiler> compiler;
-    std::mutex compiler_mutex;
-    // if a command is provided on the command line, no REPL just run the compiler on it
-    if (!cmd.empty()) {
-      compiler = std::make_unique<Compiler>(game_version);
-      compiler->run_front_end_on_string(cmd);
-      return 0;
-    }
-    compiler = std::make_unique<Compiler>(game_version, username, std::make_unique<ReplWrapper>());
-    if (repl_config) {
-      compiler->update_via_config_file(repl_config.value(), game);
-    }
-    // Start nREPL Server
+    compiler = std::make_unique<Compiler>(
+        game_version, username,
+        std::make_unique<REPL::Wrapper>(username, repl_config, startup_file));
+    // Start nREPL Server if it spun up successfully
     if (repl_server_ok) {
       nrepl_thread = std::thread([&]() {
         while (!shutdown_callback()) {
@@ -151,23 +147,7 @@ int main(int argc, char** argv) {
         }
       });
     }
-    // Run automatic forms if applicable
-    // - this should probably be deprecated in favor of the `startup.gc` file
-    if (user_startup_commands.empty() && (auto_debug || auto_listen)) {
-      user_startup_commands.push_back("(lt)");
-    }
-    if (user_startup_commands.empty() && auto_debug) {
-      std::lock_guard<std::mutex> lock(compiler_mutex);
-      status = compiler->handle_repl_string("(dbgc)");
-      user_startup_commands.push_back("(dbgc)");
-    }
-
-    if (!user_startup_commands.empty()) {
-      std::lock_guard<std::mutex> lock(compiler_mutex);
-      for (const auto& cmd : user_startup_commands) {
-        status = compiler->handle_repl_string(cmd);
-      }
-    }
+    repl_startup_func();
 
     // Poll Terminal
     while (status != ReplStatus::WANT_EXIT) {
@@ -177,18 +157,13 @@ int main(int argc, char** argv) {
         if (compiler) {
           compiler->save_repl_history();
         }
-        compiler =
-            std::make_unique<Compiler>(game_version, username, std::make_unique<ReplWrapper>());
-        if (repl_config) {
-          compiler->update_via_config_file(repl_config.value(), game);
-        }
-        if (!startup_cmd.empty()) {
-          compiler->handle_repl_string(startup_cmd);
-          // reset to prevent re-executing on manual reload
-          startup_cmd = "";
-        }
+        compiler = std::make_unique<Compiler>(
+            game_version, username,
+            std::make_unique<REPL::Wrapper>(username, repl_config, startup_file));
         status = ReplStatus::OK;
+        repl_startup_func();
       }
+      // process user input
       std::string input_from_stdin = compiler->get_repl_input();
       if (!input_from_stdin.empty()) {
         // lock, while we compile
@@ -201,6 +176,8 @@ int main(int argc, char** argv) {
     status = ReplStatus::WANT_EXIT;
   }
 
+  // TODO - investigate why there is such a delay when exitting
+
   // Cleanup
   if (repl_server_ok) {
     repl_server.shutdown_server();
diff --git a/test/offline/framework/execution.cpp b/test/offline/framework/execution.cpp
index 23e49a6911..65cfda2aba 100644
--- a/test/offline/framework/execution.cpp
+++ b/test/offline/framework/execution.cpp
@@ -1,6 +1,5 @@
 #include "execution.h"
 
-#include "common/util/diff.h"
 #include "common/util/string_util.h"
 
 #include "goalc/compiler/Compiler.h"
@@ -36,7 +35,7 @@ void decompile(OfflineTestDecompiler& dc,
 std::string clean_decompilation_code(const std::string& in, const bool leave_comments = false) {
   std::string out = in;
   if (!leave_comments) {
-    std::vector<std::string> lines = split_string(in);
+    std::vector<std::string> lines = str_util::split(in);
     // Remove all lines that are comments
     // comments are added only by us, meaning this _should_ be consistent
     std::vector<std::string>::iterator line_itr = lines.begin();
@@ -82,7 +81,7 @@ OfflineTestCompareResult compare(OfflineTestDecompiler& dc,
     compare_result.total_files++;
     compare_result.total_lines += str_util::line_count(result);
     if (result != ref) {
-      compare_result.failing_files.push_back({file.unique_name, diff_strings(ref, result)});
+      compare_result.failing_files.push_back({file.unique_name, str_util::diff(ref, result)});
       compare_result.total_pass = false;
       if (config.dump_mode) {
         auto failure_dir = file_util::get_jak_project_dir() / "failures";
diff --git a/test/offline/framework/orchestration.cpp b/test/offline/framework/orchestration.cpp
index eeeaae86cb..68d95a219b 100644
--- a/test/offline/framework/orchestration.cpp
+++ b/test/offline/framework/orchestration.cpp
@@ -311,11 +311,11 @@ void OfflineTestThreadManager::print_current_test_status(const OfflineTestConfig
   fmt::print("\x1b[{}A", lines_to_clear);  // move n lines up
   fmt::print("\e[?25l");                   // hide the cursor
   int threads_shown = 0;
-  for (int i = 0; i < statuses.size() && threads_shown < threads_to_display; i++) {
+  for (int i = 0; i < (int)statuses.size() && threads_shown < threads_to_display; i++) {
     const auto& status = statuses.at(i);
     // Skip completed threads if there are potential in-progress ones to show
     if (threads_hidden != 0 && !status->in_progress() &&
-        (statuses.size() - i) > threads_to_display) {
+        ((int)statuses.size() - i) > threads_to_display) {
       continue;
     }