diff --git a/CHANGELOG.md b/CHANGELOG.md
index 51d928d..3a86565 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -1,5 +1,8 @@
 # Changelog
 
+## [0.4.1] - 2023-02-21
+- Fixed bug causing the loading of updated plugins to fail.
+
 ## [0.4.0] - 2023-01-26
 - Added manual plugin installation helper.
 - Analyze the program by default, if provided, when entering the REPL with pyhidra.
@@ -55,7 +58,8 @@
 ## 0.1.0 - 2021-06-14
 - Initial release
 
-[Unreleased]: https://github.com/dod-cyber-crime-center/pyhidra/compare/0.4.0...HEAD
+[Unreleased]: https://github.com/dod-cyber-crime-center/pyhidra/compare/0.4.1...HEAD
+[0.4.1]: https://github.com/dod-cyber-crime-center/pyhidra/compare/0.4.0...0.4.1
 [0.4.0]: https://github.com/dod-cyber-crime-center/pyhidra/compare/0.3.0...0.4.0
 [0.3.0]: https://github.com/dod-cyber-crime-center/pyhidra/compare/0.2.1...0.3.0
 [0.2.1]: https://github.com/dod-cyber-crime-center/pyhidra/compare/0.2.0...0.2.1
diff --git a/pyhidra/__init__.py b/pyhidra/__init__.py
index 417ca28..aa31b5e 100644
--- a/pyhidra/__init__.py
+++ b/pyhidra/__init__.py
@@ -1,5 +1,5 @@
 
-__version__ = "0.4.0"
+__version__ = "0.4.1"
 
 # Expose API
 from .core import run_script, start, open_program
diff --git a/pyhidra/__main__.py b/pyhidra/__main__.py
index 042d646..1631434 100644
--- a/pyhidra/__main__.py
+++ b/pyhidra/__main__.py
@@ -70,7 +70,7 @@ def func(self):
                 self.project_path,
                 self.project_name,
                 self.verbose,
-                not self.skip_analsis
+                not self.skip_analysis
             )
             with pyhidra.core._flat_api(*args) as api:
                 _interpreter(api)
diff --git a/pyhidra/launcher.py b/pyhidra/launcher.py
index d03b569..95b187e 100644
--- a/pyhidra/launcher.py
+++ b/pyhidra/launcher.py
@@ -203,6 +203,19 @@ def start(self):
 
         jvm = _get_libjvm_path(self.java_home)
 
+        pyhidra_details = ExtensionDetails(
+            name="pyhidra",
+            description="Native Python Plugin",
+            author="Department of Defense Cyber Crime Center (DC3)",
+            plugin_version=__version__,
+        )
+
+        # uninstall any outdated plugins before starting the JVM to ensure they are loaded correctly
+        self._uninstall_old_plugin(pyhidra_details)
+
+        for _, details in self._plugins:
+            self._uninstall_old_plugin(details)
+
         jpype.startJVM(
             str(jvm),
             *self.vm_args,
@@ -221,12 +234,7 @@ def start(self):
 
         # install the Pyhidra plugin.
         from pyhidra.java import plugin
-        needs_reload = self._install_plugin(Path(plugin.__file__).parent, ExtensionDetails(
-            name="pyhidra",
-            description="Native Python Plugin",
-            author="Department of Defense Cyber Crime Center (DC3)",
-            plugin_version=__version__,
-        ))
+        needs_reload = self._install_plugin(Path(plugin.__file__).parent, pyhidra_details)
 
         if needs_reload:
             # "restart" Ghidra
@@ -237,6 +245,14 @@ def start(self):
         from pyhidra.java.plugin.plugin import PyPhidraPlugin
         PyPhidraPlugin.register()
 
+        # Add extra class paths
+        # Do this before installing plugins incase dependencies are needed
+        if self.class_files:
+            from java.lang import ClassLoader
+            gcl = ClassLoader.getSystemClassLoader()
+            for path in self.class_files:
+                gcl.addPath(path)
+
         # Install extra plugins.
         for source_path, details in self._plugins:
             needs_reload = self._install_plugin(source_path, details) or needs_reload
@@ -245,13 +261,6 @@ def start(self):
             # "restart" Ghidra
             self.layout = GhidraLauncher.initializeGhidraEnvironment()
 
-        # Add extra class paths.
-        if self.class_files:
-            from java.lang import ClassLoader
-            gcl = ClassLoader.getSystemClassLoader()
-            for path in self.class_files:
-                gcl.addPath(path)
-
         # import properties to register the property customizer
         from . import properties as _
 
@@ -280,24 +289,34 @@ def uninstall_plugin(self, plugin_name: str):
                 logger.exception(msg)
                 self._report_fatal_error(title, msg)
 
-    def _install_plugin(self, source_path: Path, details: ExtensionDetails):
+    def _uninstall_old_plugin(self, details: ExtensionDetails):
         """
-        Compiles and installs a Ghidra extension.
-        Automatically updates old plugin installation if it exists.
+        Automatically uninstalls an outdated plugin if it exists.
         """
         plugin_name = details.name
         path = self.get_install_path(plugin_name)
         ext = path / "extension.properties"
         manifest = path / "Module.manifest"
-        root = source_path
 
         # Uninstall old version.
         if manifest.exists() and ext.exists():
             orig_details = ExtensionDetails.from_file(ext)
-            if not orig_details.plugin_version or orig_details.plugin_version < details.plugin_version:
+            if not orig_details.plugin_version or orig_details.plugin_version != details.plugin_version:
                 self.uninstall_plugin(plugin_name)
                 logger.info(f"Uninstalled older plugin: {plugin_name} {orig_details.plugin_version}")
 
+
+    def _install_plugin(self, source_path: Path, details: ExtensionDetails):
+        """
+        Compiles and installs a Ghidra extension.
+        Automatically updates old plugin installation if it exists.
+        """
+        plugin_name = details.name
+        path = self.get_install_path(plugin_name)
+        ext = path / "extension.properties"
+        manifest = path / "Module.manifest"
+        root = source_path
+
         if not manifest.exists():
             jar_path = path / "lib" / (plugin_name + ".jar")
             java_compile(root.parent, jar_path)