diff --git a/external-deps/python-lsp-server/.gitrepo b/external-deps/python-lsp-server/.gitrepo
index 3df24fa3919..5c41c7a77b5 100644
--- a/external-deps/python-lsp-server/.gitrepo
+++ b/external-deps/python-lsp-server/.gitrepo
@@ -4,9 +4,9 @@
 ; git-subrepo command. See https://github.com/git-commands/git-subrepo#readme
 ;
 [subrepo]
-	remote = https://github.com/python-lsp/python-lsp-server.git
-	branch = develop
-	commit = 5a383df418d2800b5abc5dd3a43b3061026fda07
-	parent = 71e053bf7d815c0176974f9c9d5031b64946a8d9
+	remote = /Users/rclary/Documents/Repos/python-lsp-server
+	branch = ppm-syspath
+	commit = 976bcfec3ff762af735108bfcba433ae6f8c74c1
+	parent = 6f34783f0e236d3285f066c29ce22aecded1035e
 	method = merge
-	cmdver = 0.4.3
+	cmdver = 0.4.6
diff --git a/external-deps/python-lsp-server/CONFIGURATION.md b/external-deps/python-lsp-server/CONFIGURATION.md
index acf8a85fb40..bd746f767de 100644
--- a/external-deps/python-lsp-server/CONFIGURATION.md
+++ b/external-deps/python-lsp-server/CONFIGURATION.md
@@ -20,6 +20,7 @@ This server can be configured using the `workspace/didChangeConfiguration` metho
 | `pylsp.plugins.flake8.select` | `array` of unique `string` items | List of errors and warnings to enable. | `null` |
 | `pylsp.plugins.jedi.auto_import_modules` | `array` of `string` items | List of module names for jedi.settings.auto_import_modules. | `["numpy"]` |
 | `pylsp.plugins.jedi.extra_paths` | `array` of `string` items | Define extra paths for jedi.Script. | `[]` |
+| `pylsp.plugins.jedi.prioritize` | `boolean` | Whether to place extra_paths at the beginning (true) or end (false) of `sys.path` | `false` |
 | `pylsp.plugins.jedi.env_vars` | `object` | Define environment variables for jedi.Script and Jedi.names. | `null` |
 | `pylsp.plugins.jedi.environment` | `string` | Define environment for jedi.Script and Jedi.names. | `null` |
 | `pylsp.plugins.jedi_completion.enabled` | `boolean` | Enable or disable the plugin. | `true` |
diff --git a/external-deps/python-lsp-server/pylsp/config/schema.json b/external-deps/python-lsp-server/pylsp/config/schema.json
index ba1d36f8fc8..43b87e3c17d 100644
--- a/external-deps/python-lsp-server/pylsp/config/schema.json
+++ b/external-deps/python-lsp-server/pylsp/config/schema.json
@@ -143,6 +143,11 @@
       },
       "description": "Define extra paths for jedi.Script."
     },
+    "pylsp.plugins.jedi.prioritize": {
+      "type": "boolean",
+      "default": false,
+      "description": "Whether to place extra_paths at the beginning (true) or end (false) of `sys.path`"
+    },
     "pylsp.plugins.jedi.env_vars": {
       "type": [
         "object",
@@ -500,4 +505,4 @@
       "description": "The name of the folder in which rope stores project configurations and data.  Pass `null` for not using such a folder at all."
     }
   }
-}
\ No newline at end of file
+}
diff --git a/external-deps/python-lsp-server/pylsp/workspace.py b/external-deps/python-lsp-server/pylsp/workspace.py
index c1b32f20d72..0baeb5d3837 100644
--- a/external-deps/python-lsp-server/pylsp/workspace.py
+++ b/external-deps/python-lsp-server/pylsp/workspace.py
@@ -507,6 +507,7 @@ def jedi_script(self, position=None, use_document_path=False):
         extra_paths = []
         environment_path = None
         env_vars = None
+        prioritize = False
 
         if self._config:
             jedi_settings = self._config.plugin_settings(
@@ -523,9 +524,10 @@ def jedi_script(self, position=None, use_document_path=False):
 
             extra_paths = jedi_settings.get("extra_paths") or []
             env_vars = jedi_settings.get("env_vars")
+            prioritize = jedi_settings.get("prioritize")
 
-        # Drop PYTHONPATH from env_vars before creating the environment because that makes
-        # Jedi throw an error.
+        # Drop PYTHONPATH from env_vars before creating the environment because
+        # to ensure that Jedi can startup properly without module name collision.
         if env_vars is None:
             env_vars = os.environ.copy()
         env_vars.pop("PYTHONPATH", None)
@@ -535,7 +537,10 @@ def jedi_script(self, position=None, use_document_path=False):
             if environment_path
             else None
         )
-        sys_path = self.sys_path(environment_path, env_vars=env_vars) + extra_paths
+        if prioritize:
+            sys_path = extra_paths + self.sys_path(environment_path, env_vars)
+        else:
+            sys_path = self.sys_path(environment_path, env_vars) + extra_paths
         project_path = self._workspace.root_path
 
         # Extend sys_path with document's path if requested
@@ -571,8 +576,8 @@ def get_enviroment(self, environment_path=None, env_vars=None):
         return environment
 
     def sys_path(self, environment_path=None, env_vars=None):
+        # TODO: when safe to break API, remove this method.
         # Copy our extra sys path
-        # TODO: when safe to break API, use env_vars explicitly to pass to create_environment
         path = list(self._extra_sys_path)
         environment = self.get_enviroment(
             environment_path=environment_path, env_vars=env_vars