diff --git a/docs/public/schemas/fastmcp.json/latest.json b/docs/public/schemas/fastmcp.json/latest.json
index 81d0ad754..c28a50452 100644
--- a/docs/public/schemas/fastmcp.json/latest.json
+++ b/docs/public/schemas/fastmcp.json/latest.json
@@ -243,17 +243,25 @@
         "editable": {
           "anyOf": [
             {
-              "type": "string"
+              "items": {
+                "type": "string"
+              },
+              "type": "array"
             },
             {
               "type": "null"
             }
           ],
           "default": null,
-          "description": "Directory to install in editable mode",
+          "description": "Directories to install in editable mode",
           "examples": [
-            ".",
-            "../my-package"
+            [
+              ".",
+              "../my-package"
+            ],
+            [
+              "/path/to/package"
+            ]
           ],
           "title": "Editable"
         }
diff --git a/docs/public/schemas/fastmcp.json/v1.json b/docs/public/schemas/fastmcp.json/v1.json
index 81d0ad754..c28a50452 100644
--- a/docs/public/schemas/fastmcp.json/v1.json
+++ b/docs/public/schemas/fastmcp.json/v1.json
@@ -243,17 +243,25 @@
         "editable": {
           "anyOf": [
             {
-              "type": "string"
+              "items": {
+                "type": "string"
+              },
+              "type": "array"
             },
             {
               "type": "null"
             }
           ],
           "default": null,
-          "description": "Directory to install in editable mode",
+          "description": "Directories to install in editable mode",
           "examples": [
-            ".",
-            "../my-package"
+            [
+              ".",
+              "../my-package"
+            ],
+            [
+              "/path/to/package"
+            ]
           ],
           "title": "Editable"
         }
diff --git a/src/fastmcp/cli/claude.py b/src/fastmcp/cli/claude.py
index fa4d529de..8873a3a7a 100644
--- a/src/fastmcp/cli/claude.py
+++ b/src/fastmcp/cli/claude.py
@@ -34,7 +34,7 @@ def update_claude_config(
     file_spec: str,
     server_name: str,
     *,
-    with_editable: Path | None = None,
+    with_editable: list[Path] | None = None,
     with_packages: list[str] | None = None,
     env_vars: dict[str, str] | None = None,
 ) -> bool:
@@ -43,7 +43,7 @@ def update_claude_config(
     Args:
         file_spec: Path to the server file, optionally with :object suffix
         server_name: Name for the server in Claude's config
-        with_editable: Optional directory to install in editable mode
+        with_editable: Optional list of directories to install in editable mode
         with_packages: Optional list of additional packages to install
         env_vars: Optional dictionary of environment variables. These are merged with
             any existing variables, with new values taking precedence.
@@ -101,7 +101,7 @@ def update_claude_config(
         # Build uv run command using Environment.build_uv_args()
         env_config = Environment(
             dependencies=deduplicated_packages,
-            editable=[str(with_editable)] if with_editable else None,
+            editable=[str(p) for p in with_editable] if with_editable else None,
         )
         args = env_config.build_uv_args()
 
diff --git a/src/fastmcp/cli/cli.py b/src/fastmcp/cli/cli.py
index aba034e20..84611d0a3 100644
--- a/src/fastmcp/cli/cli.py
+++ b/src/fastmcp/cli/cli.py
@@ -126,20 +126,21 @@ async def dev(
     server_spec: str | None = None,
     *,
     with_editable: Annotated[
-        Path | None,
+        list[Path] | None,
         cyclopts.Parameter(
-            name=["--with-editable", "-e"],
-            help="Directory containing pyproject.toml to install in editable mode",
+            "--with-editable",
+            help="Directory containing pyproject.toml to install in editable mode (can be used multiple times)",
+            negative="",
         ),
     ] = None,
     with_packages: Annotated[
-        list[str],
+        list[str] | None,
         cyclopts.Parameter(
             "--with",
-            help="Additional packages to install",
+            help="Additional packages to install (can be used multiple times)",
             negative="",
         ),
-    ] = [],
+    ] = None,
     inspector_version: Annotated[
         str | None,
         cyclopts.Parameter(
@@ -188,6 +189,9 @@ async def dev(
     Args:
         server_spec: Python file to run, optionally with :object suffix, or None to auto-detect fastmcp.json
     """
+    # Convert None to empty lists for list parameters
+    with_editable = with_editable or []
+    with_packages = with_packages or []
     from pathlib import Path
 
     from fastmcp.utilities.fastmcp_config import FastMCPConfig
@@ -229,13 +233,9 @@ async def dev(
                 if config.environment.requirements
                 else None
             )
-            # Note: config.environment.editable is a list, but CLI only supports single path
-            # Take the first editable path if available
-            with_editable = with_editable or (
-                Path(config.environment.editable[0])
-                if config.environment.editable and config.environment.editable[0]
-                else None
-            )
+            # Merge editable paths from config with CLI args
+            if config.environment.editable and not with_editable:
+                with_editable = [Path(p) for p in config.environment.editable]
 
             # Merge packages from both sources
             if config.environment.dependencies:
@@ -256,7 +256,7 @@ async def dev(
         "Starting dev server",
         extra={
             "server_spec": server_spec,
-            "with_editable": str(with_editable) if with_editable else None,
+            "with_editable": [str(p) for p in with_editable] if with_editable else None,
             "with_packages": with_packages,
             "ui_port": ui_port,
             "server_port": server_port,
@@ -305,7 +305,7 @@ async def dev(
             dependencies=with_packages if with_packages else None,
             requirements=str(with_requirements) if with_requirements else None,
             project=str(project) if project else None,
-            editable=[str(with_editable)] if with_editable else None,
+            editable=[str(p) for p in with_editable] if with_editable else None,
         )
         uv_cmd = ["uv"] + env_config.build_uv_args(["fastmcp", "run", server_spec])
 
@@ -396,13 +396,13 @@ async def run(
         ),
     ] = None,
     with_packages: Annotated[
-        list[str],
+        list[str] | None,
         cyclopts.Parameter(
             "--with",
             help="Additional packages to install (can be used multiple times)",
             negative="",
         ),
-    ] = [],
+    ] = None,
     project: Annotated[
         Path | None,
         cyclopts.Parameter(
@@ -450,6 +450,8 @@ async def run(
     Args:
         server_spec: Python file, object specification (file:obj), config file, URL, or None to auto-detect
     """
+    # Convert None to empty lists for list parameters
+    with_packages = with_packages or []
     # Load configuration if needed
     from pathlib import Path
 
@@ -631,13 +633,13 @@ async def inspect(
         ),
     ] = None,
     with_packages: Annotated[
-        list[str],
+        list[str] | None,
         cyclopts.Parameter(
             "--with",
             help="Additional packages to install (can be used multiple times)",
             negative="",
         ),
-    ] = [],
+    ] = None,
     project: Annotated[
         Path | None,
         cyclopts.Parameter(
@@ -670,6 +672,8 @@ async def inspect(
     Args:
         server_spec: Python file to inspect, optionally with :object suffix, or fastmcp.json
     """
+    # Convert None to empty lists for list parameters
+    with_packages = with_packages or []
     from pathlib import Path
 
     from fastmcp.utilities.fastmcp_config import FastMCPConfig
diff --git a/src/fastmcp/cli/install/claude_code.py b/src/fastmcp/cli/install/claude_code.py
index 472a34c54..aaa07503c 100644
--- a/src/fastmcp/cli/install/claude_code.py
+++ b/src/fastmcp/cli/install/claude_code.py
@@ -75,7 +75,7 @@ def install_claude_code(
     server_object: str | None,
     name: str,
     *,
-    with_editable: Path | None = None,
+    with_editable: list[Path] | None = None,
     with_packages: list[str] | None = None,
     env_vars: dict[str, str] | None = None,
     python_version: str | None = None,
@@ -88,7 +88,7 @@ def install_claude_code(
         file: Path to the server file
         server_object: Optional server object name (for :object suffix)
         name: Name for the server in Claude Code
-        with_editable: Optional directory to install in editable mode
+        with_editable: Optional list of directories to install in editable mode
         with_packages: Optional list of additional packages to install
         env_vars: Optional dictionary of environment variables
         python_version: Optional Python version to use
@@ -121,7 +121,7 @@ def install_claude_code(
         dependencies=deduplicated_packages,
         requirements=str(with_requirements) if with_requirements else None,
         project=str(project) if project else None,
-        editable=[str(with_editable)] if with_editable else None,
+        editable=[str(p) for p in with_editable] if with_editable else None,
     )
     args = env_config.build_uv_args()
 
@@ -171,28 +171,29 @@ async def claude_code_command(
         ),
     ] = None,
     with_editable: Annotated[
-        Path | None,
+        list[Path] | None,
         cyclopts.Parameter(
-            name=["--with-editable", "-e"],
-            help="Directory with pyproject.toml to install in editable mode",
+            "--with-editable",
+            help="Directory with pyproject.toml to install in editable mode (can be used multiple times)",
+            negative="",
         ),
     ] = None,
     with_packages: Annotated[
-        list[str],
+        list[str] | None,
         cyclopts.Parameter(
             "--with",
-            help="Additional packages to install",
+            help="Additional packages to install (can be used multiple times)",
             negative="",
         ),
-    ] = [],
+    ] = None,
     env_vars: Annotated[
-        list[str],
+        list[str] | None,
         cyclopts.Parameter(
             "--env",
-            help="Environment variables in KEY=VALUE format",
+            help="Environment variables in KEY=VALUE format (can be used multiple times)",
             negative="",
         ),
-    ] = [],
+    ] = None,
     env_file: Annotated[
         Path | None,
         cyclopts.Parameter(
@@ -227,6 +228,10 @@ async def claude_code_command(
     Args:
         server_spec: Python file to install, optionally with :object suffix
     """
+    # Convert None to empty lists for list parameters
+    with_editable = with_editable or []
+    with_packages = with_packages or []
+    env_vars = env_vars or []
     file, server_object, name, packages, env_dict = await process_common_args(
         server_spec, server_name, with_packages, env_vars, env_file
     )
diff --git a/src/fastmcp/cli/install/claude_desktop.py b/src/fastmcp/cli/install/claude_desktop.py
index 69e543415..28ce20eee 100644
--- a/src/fastmcp/cli/install/claude_desktop.py
+++ b/src/fastmcp/cli/install/claude_desktop.py
@@ -40,7 +40,7 @@ def install_claude_desktop(
     server_object: str | None,
     name: str,
     *,
-    with_editable: Path | None = None,
+    with_editable: list[Path] | None = None,
     with_packages: list[str] | None = None,
     env_vars: dict[str, str] | None = None,
     python_version: str | None = None,
@@ -53,7 +53,7 @@ def install_claude_desktop(
         file: Path to the server file
         server_object: Optional server object name (for :object suffix)
         name: Name for the server in Claude's config
-        with_editable: Optional directory to install in editable mode
+        with_editable: Optional list of directories to install in editable mode
         with_packages: Optional list of additional packages to install
         env_vars: Optional dictionary of environment variables
         python_version: Optional Python version to use
@@ -86,7 +86,7 @@ def install_claude_desktop(
         dependencies=deduplicated_packages,
         requirements=str(with_requirements) if with_requirements else None,
         project=str(project) if project else None,
-        editable=[str(with_editable)] if with_editable else None,
+        editable=[str(p) for p in with_editable] if with_editable else None,
     )
     args = env_config.build_uv_args()
 
@@ -143,28 +143,29 @@ async def claude_desktop_command(
         ),
     ] = None,
     with_editable: Annotated[
-        Path | None,
+        list[Path] | None,
         cyclopts.Parameter(
-            name=["--with-editable", "-e"],
-            help="Directory with pyproject.toml to install in editable mode",
+            "--with-editable",
+            help="Directory with pyproject.toml to install in editable mode (can be used multiple times)",
+            negative="",
         ),
     ] = None,
     with_packages: Annotated[
-        list[str],
+        list[str] | None,
         cyclopts.Parameter(
             "--with",
-            help="Additional packages to install",
+            help="Additional packages to install (can be used multiple times)",
             negative="",
         ),
-    ] = [],
+    ] = None,
     env_vars: Annotated[
-        list[str],
+        list[str] | None,
         cyclopts.Parameter(
             "--env",
-            help="Environment variables in KEY=VALUE format",
+            help="Environment variables in KEY=VALUE format (can be used multiple times)",
             negative="",
         ),
-    ] = [],
+    ] = None,
     env_file: Annotated[
         Path | None,
         cyclopts.Parameter(
@@ -199,6 +200,10 @@ async def claude_desktop_command(
     Args:
         server_spec: Python file to install, optionally with :object suffix
     """
+    # Convert None to empty lists for list parameters
+    with_editable = with_editable or []
+    with_packages = with_packages or []
+    env_vars = env_vars or []
     file, server_object, name, with_packages, env_dict = await process_common_args(
         server_spec, server_name, with_packages, env_vars, env_file
     )
diff --git a/src/fastmcp/cli/install/cursor.py b/src/fastmcp/cli/install/cursor.py
index 472dd610f..bbb94a872 100644
--- a/src/fastmcp/cli/install/cursor.py
+++ b/src/fastmcp/cli/install/cursor.py
@@ -71,7 +71,7 @@ def install_cursor_workspace(
     name: str,
     workspace_path: Path,
     *,
-    with_editable: Path | None = None,
+    with_editable: list[Path] | None = None,
     with_packages: list[str] | None = None,
     env_vars: dict[str, str] | None = None,
     python_version: str | None = None,
@@ -85,7 +85,7 @@ def install_cursor_workspace(
         server_object: Optional server object name (for :object suffix)
         name: Name for the server in Cursor
         workspace_path: Path to the workspace directory
-        with_editable: Optional directory to install in editable mode
+        with_editable: Optional list of directories to install in editable mode
         with_packages: Optional list of additional packages to install
         env_vars: Optional dictionary of environment variables
         python_version: Optional Python version to use
@@ -120,7 +120,7 @@ def install_cursor_workspace(
         dependencies=deduplicated_packages,
         requirements=str(with_requirements.resolve()) if with_requirements else None,
         project=str(project.resolve()) if project else None,
-        editable=[str(with_editable.resolve())] if with_editable else None,
+        editable=[str(p.resolve()) for p in with_editable] if with_editable else None,
     )
     args = env_config.build_uv_args()
 
@@ -161,7 +161,7 @@ def install_cursor(
     server_object: str | None,
     name: str,
     *,
-    with_editable: Path | None = None,
+    with_editable: list[Path] | None = None,
     with_packages: list[str] | None = None,
     env_vars: dict[str, str] | None = None,
     python_version: str | None = None,
@@ -175,7 +175,7 @@ def install_cursor(
         file: Path to the server file
         server_object: Optional server object name (for :object suffix)
         name: Name for the server in Cursor
-        with_editable: Optional directory to install in editable mode
+        with_editable: Optional list of directories to install in editable mode
         with_packages: Optional list of additional packages to install
         env_vars: Optional dictionary of environment variables
         python_version: Optional Python version to use
@@ -200,7 +200,7 @@ def install_cursor(
         dependencies=deduplicated_packages,
         requirements=str(with_requirements.resolve()) if with_requirements else None,
         project=str(project.resolve()) if project else None,
-        editable=[str(with_editable.resolve())] if with_editable else None,
+        editable=[str(p.resolve()) for p in with_editable] if with_editable else None,
     )
     args = env_config.build_uv_args()
 
@@ -262,28 +262,29 @@ async def cursor_command(
         ),
     ] = None,
     with_editable: Annotated[
-        Path | None,
+        list[Path] | None,
         cyclopts.Parameter(
-            name=["--with-editable", "-e"],
-            help="Directory with pyproject.toml to install in editable mode",
+            "--with-editable",
+            help="Directory with pyproject.toml to install in editable mode (can be used multiple times)",
+            negative="",
         ),
     ] = None,
     with_packages: Annotated[
-        list[str],
+        list[str] | None,
         cyclopts.Parameter(
             "--with",
-            help="Additional packages to install",
+            help="Additional packages to install (can be used multiple times)",
             negative="",
         ),
-    ] = [],
+    ] = None,
     env_vars: Annotated[
-        list[str],
+        list[str] | None,
         cyclopts.Parameter(
             "--env",
-            help="Environment variables in KEY=VALUE format",
+            help="Environment variables in KEY=VALUE format (can be used multiple times)",
             negative="",
         ),
-    ] = [],
+    ] = None,
     env_file: Annotated[
         Path | None,
         cyclopts.Parameter(
@@ -325,6 +326,10 @@ async def cursor_command(
     Args:
         server_spec: Python file to install, optionally with :object suffix
     """
+    # Convert None to empty lists for list parameters
+    with_editable = with_editable or []
+    with_packages = with_packages or []
+    env_vars = env_vars or []
     file, server_object, name, with_packages, env_dict = await process_common_args(
         server_spec, server_name, with_packages, env_vars, env_file
     )
diff --git a/src/fastmcp/cli/install/mcp_json.py b/src/fastmcp/cli/install/mcp_json.py
index 9315c40ef..42696ae6c 100644
--- a/src/fastmcp/cli/install/mcp_json.py
+++ b/src/fastmcp/cli/install/mcp_json.py
@@ -22,7 +22,7 @@ def install_mcp_json(
     server_object: str | None,
     name: str,
     *,
-    with_editable: Path | None = None,
+    with_editable: list[Path] | None = None,
     with_packages: list[str] | None = None,
     env_vars: dict[str, str] | None = None,
     copy: bool = False,
@@ -36,7 +36,7 @@ def install_mcp_json(
         file: Path to the server file
         server_object: Optional server object name (for :object suffix)
         name: Name for the server in MCP config
-        with_editable: Optional directory to install in editable mode
+        with_editable: Optional list of directories to install in editable mode
         with_packages: Optional list of additional packages to install
         env_vars: Optional dictionary of environment variables
         copy: If True, copy to clipboard instead of printing to stdout
@@ -61,7 +61,7 @@ def install_mcp_json(
             dependencies=deduplicated_packages,
             requirements=str(with_requirements) if with_requirements else None,
             project=str(project) if project else None,
-            editable=[str(with_editable)] if with_editable else None,
+            editable=[str(p) for p in with_editable] if with_editable else None,
         )
         args = env_config.build_uv_args()
 
@@ -116,28 +116,29 @@ async def mcp_json_command(
         ),
     ] = None,
     with_editable: Annotated[
-        Path | None,
+        list[Path] | None,
         cyclopts.Parameter(
-            name=["--with-editable", "-e"],
-            help="Directory with pyproject.toml to install in editable mode",
+            "--with-editable",
+            help="Directory with pyproject.toml to install in editable mode (can be used multiple times)",
+            negative="",
         ),
     ] = None,
     with_packages: Annotated[
-        list[str],
+        list[str] | None,
         cyclopts.Parameter(
             "--with",
-            help="Additional packages to install",
+            help="Additional packages to install (can be used multiple times)",
             negative="",
         ),
-    ] = [],
+    ] = None,
     env_vars: Annotated[
-        list[str],
+        list[str] | None,
         cyclopts.Parameter(
             "--env",
-            help="Environment variables in KEY=VALUE format",
+            help="Environment variables in KEY=VALUE format (can be used multiple times)",
             negative="",
         ),
-    ] = [],
+    ] = None,
     env_file: Annotated[
         Path | None,
         cyclopts.Parameter(
@@ -180,6 +181,10 @@ async def mcp_json_command(
     Args:
         server_spec: Python file to install, optionally with :object suffix
     """
+    # Convert None to empty lists for list parameters
+    with_editable = with_editable or []
+    with_packages = with_packages or []
+    env_vars = env_vars or []
     file, server_object, name, packages, env_dict = await process_common_args(
         server_spec, server_name, with_packages, env_vars, env_file
     )
diff --git a/src/fastmcp/cli/install/shared.py b/src/fastmcp/cli/install/shared.py
index 2f92fbd89..6db83403f 100644
--- a/src/fastmcp/cli/install/shared.py
+++ b/src/fastmcp/cli/install/shared.py
@@ -29,14 +29,17 @@ def parse_env_var(env_var: str) -> tuple[str, str]:
 async def process_common_args(
     server_spec: str,
     server_name: str | None,
-    with_packages: list[str],
-    env_vars: list[str],
+    with_packages: list[str] | None,
+    env_vars: list[str] | None,
     env_file: Path | None,
 ) -> tuple[Path, str | None, str, list[str], dict[str, str] | None]:
     """Process common arguments shared by all install commands.
 
     Handles both fastmcp.json config files and traditional file.py:object syntax.
     """
+    # Convert None to empty lists for list parameters
+    with_packages = with_packages or []
+    env_vars = env_vars or []
     # Create FastMCPConfig from server_spec
     config = None
     if server_spec.endswith(".json"):
diff --git a/tests/cli/test_cursor.py b/tests/cli/test_cursor.py
index 008aff843..c5531bd8d 100644
--- a/tests/cli/test_cursor.py
+++ b/tests/cli/test_cursor.py
@@ -246,7 +246,7 @@ class TestInstallCursor:
             file=Path("/path/to/server.py"),
             server_object="custom_app",
             name="test-server",
-            with_editable=editable_path,
+            with_editable=[editable_path],
         )
 
         assert result is True
@@ -328,7 +328,7 @@ class TestCursorCommand:
             file=Path("server.py"),
             server_object=None,
             name="test-server",
-            with_editable=None,
+            with_editable=[],
             with_packages=[],
             env_vars={},
             python_version=None,