diff --git a/crates/uv-cli/src/lib.rs b/crates/uv-cli/src/lib.rs
index 56a4f0a88186..ac3704ec8e40 100644
--- a/crates/uv-cli/src/lib.rs
+++ b/crates/uv-cli/src/lib.rs
@@ -827,6 +827,16 @@ fn parse_maybe_file_path(input: &str) -> Result<Maybe<PathBuf>, String> {
     }
 }
 
+// Parse a string, mapping the empty string to `None`.
+#[allow(clippy::unnecessary_wraps)]
+fn parse_maybe_string(input: &str) -> Result<Maybe<String>, String> {
+    if input.is_empty() {
+        Ok(Maybe::None)
+    } else {
+        Ok(Maybe::Some(input.to_string()))
+    }
+}
+
 #[derive(Args)]
 #[allow(clippy::struct_excessive_bools)]
 pub struct PipCompileArgs {
@@ -967,8 +977,8 @@ pub struct PipCompileArgs {
     ///
     /// See `uv help python` for details on Python discovery and supported
     /// request formats.
-    #[arg(long, verbatim_doc_comment, help_heading = "Python options")]
-    pub python: Option<String>,
+    #[arg(long, verbatim_doc_comment, help_heading = "Python options", value_parser = parse_maybe_string)]
+    pub python: Option<Maybe<String>>,
 
     /// Install packages into the system Python environment.
     ///
@@ -1221,9 +1231,10 @@ pub struct PipSyncArgs {
         short,
         env = "UV_PYTHON",
         verbatim_doc_comment,
-        help_heading = "Python options"
+        help_heading = "Python options",
+        value_parser = parse_maybe_string,
     )]
-    pub python: Option<String>,
+    pub python: Option<Maybe<String>>,
 
     /// Install packages into the system Python environment.
     ///
@@ -1503,9 +1514,10 @@ pub struct PipInstallArgs {
         short,
         env = "UV_PYTHON",
         verbatim_doc_comment,
-        help_heading = "Python options"
+        help_heading = "Python options",
+        value_parser = parse_maybe_string,
     )]
-    pub python: Option<String>,
+    pub python: Option<Maybe<String>>,
 
     /// Install packages into the system Python environment.
     ///
@@ -1668,9 +1680,10 @@ pub struct PipUninstallArgs {
         short,
         env = "UV_PYTHON",
         verbatim_doc_comment,
-        help_heading = "Python options"
+        help_heading = "Python options",
+        value_parser = parse_maybe_string,
     )]
-    pub python: Option<String>,
+    pub python: Option<Maybe<String>>,
 
     /// Attempt to use `keyring` for authentication for remote requirements files.
     ///
@@ -1776,9 +1789,10 @@ pub struct PipFreezeArgs {
         short,
         env = "UV_PYTHON",
         verbatim_doc_comment,
-        help_heading = "Python options"
+        help_heading = "Python options",
+        value_parser = parse_maybe_string,
     )]
-    pub python: Option<String>,
+    pub python: Option<Maybe<String>>,
 
     /// List packages in the system Python environment.
     ///
@@ -1840,9 +1854,10 @@ pub struct PipListArgs {
         short,
         env = "UV_PYTHON",
         verbatim_doc_comment,
-        help_heading = "Python options"
+        help_heading = "Python options",
+        value_parser = parse_maybe_string,
     )]
-    pub python: Option<String>,
+    pub python: Option<Maybe<String>>,
 
     /// List packages in the system Python environment.
     ///
@@ -1880,9 +1895,10 @@ pub struct PipCheckArgs {
         short,
         env = "UV_PYTHON",
         verbatim_doc_comment,
-        help_heading = "Python options"
+        help_heading = "Python options",
+        value_parser = parse_maybe_string,
     )]
-    pub python: Option<String>,
+    pub python: Option<Maybe<String>>,
 
     /// Check packages in the system Python environment.
     ///
@@ -1928,9 +1944,10 @@ pub struct PipShowArgs {
         short,
         env = "UV_PYTHON",
         verbatim_doc_comment,
-        help_heading = "Python options"
+        help_heading = "Python options",
+        value_parser = parse_maybe_string,
     )]
-    pub python: Option<String>,
+    pub python: Option<Maybe<String>>,
 
     /// Show a package in the system Python environment.
     ///
@@ -1983,9 +2000,10 @@ pub struct PipTreeArgs {
         short,
         env = "UV_PYTHON",
         verbatim_doc_comment,
-        help_heading = "Python options"
+        help_heading = "Python options",
+        value_parser = parse_maybe_string,
     )]
-    pub python: Option<String>,
+    pub python: Option<Maybe<String>>,
 
     /// List packages in the system Python environment.
     ///
@@ -2118,9 +2136,10 @@ pub struct BuildArgs {
         short,
         env = "UV_PYTHON",
         verbatim_doc_comment,
-        help_heading = "Python options"
+        help_heading = "Python options",
+        value_parser = parse_maybe_string,
     )]
-    pub python: Option<String>,
+    pub python: Option<Maybe<String>>,
 
     #[command(flatten)]
     pub resolver: ResolverArgs,
@@ -2147,9 +2166,10 @@ pub struct VenvArgs {
         short,
         env = "UV_PYTHON",
         verbatim_doc_comment,
-        help_heading = "Python options"
+        help_heading = "Python options",
+        value_parser = parse_maybe_string,
     )]
-    pub python: Option<String>,
+    pub python: Option<Maybe<String>>,
 
     /// Ignore virtual environments when searching for the Python interpreter.
     ///
@@ -2435,9 +2455,10 @@ pub struct InitArgs {
         short,
         env = "UV_PYTHON",
         verbatim_doc_comment,
-        help_heading = "Python options"
+        help_heading = "Python options",
+        value_parser = parse_maybe_string,
     )]
-    pub python: Option<String>,
+    pub python: Option<Maybe<String>>,
 }
 
 #[derive(Args)]
@@ -2610,9 +2631,10 @@ pub struct RunArgs {
         short,
         env = "UV_PYTHON",
         verbatim_doc_comment,
-        help_heading = "Python options"
+        help_heading = "Python options",
+        value_parser = parse_maybe_string,
     )]
-    pub python: Option<String>,
+    pub python: Option<Maybe<String>>,
 
     /// Whether to show resolver and installer output from any environment modifications.
     ///
@@ -2752,9 +2774,10 @@ pub struct SyncArgs {
         short,
         env = "UV_PYTHON",
         verbatim_doc_comment,
-        help_heading = "Python options"
+        help_heading = "Python options",
+        value_parser = parse_maybe_string,
     )]
-    pub python: Option<String>,
+    pub python: Option<Maybe<String>>,
 }
 
 #[derive(Args)]
@@ -2795,9 +2818,10 @@ pub struct LockArgs {
         short,
         env = "UV_PYTHON",
         verbatim_doc_comment,
-        help_heading = "Python options"
+        help_heading = "Python options",
+        value_parser = parse_maybe_string,
     )]
-    pub python: Option<String>,
+    pub python: Option<Maybe<String>>,
 }
 
 #[derive(Args)]
@@ -2917,9 +2941,10 @@ pub struct AddArgs {
         short,
         env = "UV_PYTHON",
         verbatim_doc_comment,
-        help_heading = "Python options"
+        help_heading = "Python options",
+        value_parser = parse_maybe_string,
     )]
-    pub python: Option<String>,
+    pub python: Option<Maybe<String>>,
 }
 
 #[derive(Args)]
@@ -2983,9 +3008,10 @@ pub struct RemoveArgs {
         short,
         env = "UV_PYTHON",
         verbatim_doc_comment,
-        help_heading = "Python options"
+        help_heading = "Python options",
+        value_parser = parse_maybe_string,
     )]
-    pub python: Option<String>,
+    pub python: Option<Maybe<String>>,
 }
 
 #[derive(Args)]
@@ -3057,9 +3083,10 @@ pub struct TreeArgs {
         short,
         env = "UV_PYTHON",
         verbatim_doc_comment,
-        help_heading = "Python options"
+        help_heading = "Python options",
+        value_parser = parse_maybe_string,
     )]
-    pub python: Option<String>,
+    pub python: Option<Maybe<String>>,
 }
 
 #[derive(Args)]
@@ -3181,9 +3208,10 @@ pub struct ExportArgs {
         short,
         env = "UV_PYTHON",
         verbatim_doc_comment,
-        help_heading = "Python options"
+        help_heading = "Python options",
+        value_parser = parse_maybe_string,
     )]
-    pub python: Option<String>,
+    pub python: Option<Maybe<String>>,
 }
 
 #[derive(Args)]
@@ -3330,9 +3358,10 @@ pub struct ToolRunArgs {
         short,
         env = "UV_PYTHON",
         verbatim_doc_comment,
-        help_heading = "Python options"
+        help_heading = "Python options",
+        value_parser = parse_maybe_string,
     )]
-    pub python: Option<String>,
+    pub python: Option<Maybe<String>>,
 
     /// Whether to show resolver and installer output from any environment modifications.
     ///
@@ -3391,9 +3420,10 @@ pub struct ToolInstallArgs {
         short,
         env = "UV_PYTHON",
         verbatim_doc_comment,
-        help_heading = "Python options"
+        help_heading = "Python options",
+        value_parser = parse_maybe_string,
     )]
-    pub python: Option<String>,
+    pub python: Option<Maybe<String>>,
 }
 
 #[derive(Args)]
@@ -3467,9 +3497,10 @@ pub struct ToolUpgradeArgs {
         short,
         env = "UV_PYTHON",
         verbatim_doc_comment,
-        help_heading = "Python options"
+        help_heading = "Python options",
+        value_parser = parse_maybe_string,
     )]
-    pub python: Option<String>,
+    pub python: Option<Maybe<String>>,
 
     #[command(flatten)]
     pub installer: ResolverInstallerArgs,
diff --git a/crates/uv/src/settings.rs b/crates/uv/src/settings.rs
index 582e20787cc6..d8ae29071941 100644
--- a/crates/uv/src/settings.rs
+++ b/crates/uv/src/settings.rs
@@ -208,7 +208,7 @@ impl InitSettings {
             no_readme,
             no_pin_python,
             no_workspace,
-            python,
+            python: python.and_then(Maybe::into_option),
         }
     }
 }
@@ -286,7 +286,7 @@ impl RunSettings {
             package,
             no_project,
             no_sync,
-            python,
+            python: python.and_then(Maybe::into_option),
             refresh: Refresh::from(refresh),
             settings: ResolverInstallerSettings::combine(
                 resolver_installer_options(installer, build),
@@ -364,7 +364,7 @@ impl ToolRunSettings {
                 .collect(),
             isolated,
             show_resolution,
-            python,
+            python: python.and_then(Maybe::into_option),
             refresh: Refresh::from(refresh),
             settings: ResolverInstallerSettings::combine(
                 resolver_installer_options(installer, build),
@@ -424,7 +424,7 @@ impl ToolInstallSettings {
                 .into_iter()
                 .filter_map(Maybe::into_option)
                 .collect(),
-            python,
+            python: python.and_then(Maybe::into_option),
             force,
             editable,
             refresh: Refresh::from(refresh),
@@ -472,7 +472,7 @@ impl ToolUpgradeSettings {
 
         Self {
             name: if all { vec![] } else { name },
-            python,
+            python: python.and_then(Maybe::into_option),
             args,
             filesystem,
         }
@@ -744,7 +744,7 @@ impl SyncSettings {
                 Modifications::Sufficient
             },
             package,
-            python,
+            python: python.and_then(Maybe::into_option),
             refresh: Refresh::from(refresh),
             settings,
         }
@@ -778,7 +778,7 @@ impl LockSettings {
         Self {
             locked,
             frozen,
-            python,
+            python: python.and_then(Maybe::into_option),
             refresh: Refresh::from(refresh),
             settings: ResolverSettings::combine(resolver_options(resolver, build), filesystem),
         }
@@ -856,7 +856,7 @@ impl AddSettings {
             branch,
             package,
             script,
-            python,
+            python: python.and_then(Maybe::into_option),
             editable: flag(editable, no_editable),
             extras: extra.unwrap_or_default(),
             refresh: Refresh::from(refresh),
@@ -919,7 +919,7 @@ impl RemoveSettings {
             dependency_type,
             package,
             script,
-            python,
+            python: python.and_then(Maybe::into_option),
             refresh: Refresh::from(refresh),
             settings: ResolverInstallerSettings::combine(
                 resolver_installer_options(installer, build),
@@ -973,7 +973,7 @@ impl TreeSettings {
             invert: tree.invert,
             python_version,
             python_platform,
-            python,
+            python: python.and_then(Maybe::into_option),
             resolver: ResolverSettings::combine(resolver_options(resolver, build), filesystem),
         }
     }
@@ -1044,7 +1044,7 @@ impl ExportSettings {
             output_file,
             locked,
             frozen,
-            python,
+            python: python.and_then(Maybe::into_option),
             refresh: Refresh::from(refresh),
             settings: ResolverSettings::combine(resolver_options(resolver, build), filesystem),
         }
@@ -1173,7 +1173,7 @@ impl PipCompileSettings {
             refresh: Refresh::from(refresh),
             settings: PipSettings::combine(
                 PipOptions {
-                    python,
+                    python: python.and_then(Maybe::into_option),
                     system: flag(system, no_system),
                     no_build: flag(no_build, build),
                     no_binary,
@@ -1266,7 +1266,7 @@ impl PipSyncSettings {
             refresh: Refresh::from(refresh),
             settings: PipSettings::combine(
                 PipOptions {
-                    python,
+                    python: python.and_then(Maybe::into_option),
                     system: flag(system, no_system),
                     break_system_packages: flag(break_system_packages, no_break_system_packages),
                     target,
@@ -1398,7 +1398,7 @@ impl PipInstallSettings {
             refresh: Refresh::from(refresh),
             settings: PipSettings::combine(
                 PipOptions {
-                    python,
+                    python: python.and_then(Maybe::into_option),
                     system: flag(system, no_system),
                     break_system_packages: flag(break_system_packages, no_break_system_packages),
                     target,
@@ -1454,7 +1454,7 @@ impl PipUninstallSettings {
             requirement,
             settings: PipSettings::combine(
                 PipOptions {
-                    python,
+                    python: python.and_then(Maybe::into_option),
                     system: flag(system, no_system),
                     break_system_packages: flag(break_system_packages, no_break_system_packages),
                     target,
@@ -1499,7 +1499,7 @@ impl PipFreezeSettings {
             exclude_editable,
             settings: PipSettings::combine(
                 PipOptions {
-                    python,
+                    python: python.and_then(Maybe::into_option),
                     system: flag(system, no_system),
                     strict: flag(strict, no_strict),
                     ..PipOptions::default()
@@ -1542,7 +1542,7 @@ impl PipListSettings {
             format,
             settings: PipSettings::combine(
                 PipOptions {
-                    python,
+                    python: python.and_then(Maybe::into_option),
                     system: flag(system, no_system),
                     strict: flag(strict, no_strict),
                     ..PipOptions::default()
@@ -1578,7 +1578,7 @@ impl PipShowSettings {
             package,
             settings: PipSettings::combine(
                 PipOptions {
-                    python,
+                    python: python.and_then(Maybe::into_option),
                     system: flag(system, no_system),
                     strict: flag(strict, no_strict),
                     ..PipOptions::default()
@@ -1627,7 +1627,7 @@ impl PipTreeSettings {
             // Shared settings.
             shared: PipSettings::combine(
                 PipOptions {
-                    python,
+                    python: python.and_then(Maybe::into_option),
                     system: flag(system, no_system),
                     strict: flag(strict, no_strict),
                     ..PipOptions::default()
@@ -1657,7 +1657,7 @@ impl PipCheckSettings {
         Self {
             settings: PipSettings::combine(
                 PipOptions {
-                    python,
+                    python: python.and_then(Maybe::into_option),
                     system: flag(system, no_system),
                     ..PipOptions::default()
                 },
@@ -1724,7 +1724,7 @@ impl BuildSettings {
                 flag(require_hashes, no_require_hashes).unwrap_or_default(),
                 flag(verify_hashes, no_verify_hashes).unwrap_or_default(),
             ),
-            python,
+            python: python.and_then(Maybe::into_option),
             refresh: Refresh::from(refresh),
             settings: ResolverSettings::combine(resolver_options(resolver, build), filesystem),
         }
@@ -1778,7 +1778,7 @@ impl VenvSettings {
             relocatable,
             settings: PipSettings::combine(
                 PipOptions {
-                    python,
+                    python: python.and_then(Maybe::into_option),
                     system: flag(system, no_system),
                     index_strategy,
                     keyring_provider,