diff --git a/crates/uv-cli/src/options.rs b/crates/uv-cli/src/options.rs
index ba80736a0..492942f1b 100644
--- a/crates/uv-cli/src/options.rs
+++ b/crates/uv-cli/src/options.rs
@@ -1,7 +1,8 @@
 use anstream::eprintln;
 
 use uv_cache::Refresh;
-use uv_distribution_types::{ConfigSettings, PackageConfigSettings};
+use uv_configuration::UpgradeSelection;
+use uv_distribution_types::{ConfigSettings, PackageConfigSettings, Requirement};
 use uv_resolver::{ExcludeNewer, ExcludeNewerPackage, PrereleaseMode};
 use uv_settings::{Combine, PipOptions, ResolverInstallerOptions, ResolverOptions};
 use uv_warnings::owo_colors::OwoColorize;
@@ -333,8 +334,10 @@ pub fn resolver_options(
                 .filter_map(Maybe::into_option)
                 .collect()
         }),
-        upgrade: flag(upgrade, no_upgrade, "no-upgrade"),
-        upgrade_package: Some(upgrade_package),
+        upgrade: UpgradeSelection::from_args(
+            flag(upgrade, no_upgrade, "no-upgrade"),
+            upgrade_package.into_iter().map(Requirement::from).collect(),
+        ),
         index_strategy,
         keyring_provider,
         resolution,
@@ -442,12 +445,10 @@ pub fn resolver_installer_options(
                 .filter_map(Maybe::into_option)
                 .collect()
         }),
-        upgrade: flag(upgrade, no_upgrade, "upgrade"),
-        upgrade_package: if upgrade_package.is_empty() {
-            None
-        } else {
-            Some(upgrade_package)
-        },
+        upgrade: UpgradeSelection::from_args(
+            flag(upgrade, no_upgrade, "upgrade"),
+            upgrade_package.into_iter().map(Requirement::from).collect(),
+        ),
         reinstall: flag(reinstall, no_reinstall, "reinstall"),
         reinstall_package: if reinstall_package.is_empty() {
             None
diff --git a/crates/uv-configuration/src/package_options.rs b/crates/uv-configuration/src/package_options.rs
index a8654089e..f4b04a245 100644
--- a/crates/uv-configuration/src/package_options.rs
+++ b/crates/uv-configuration/src/package_options.rs
@@ -134,9 +134,57 @@ impl From<Reinstall> for Refresh {
     }
 }
 
+/// An upgrade selection as specified by a user on the command line or in a configuration file.
+#[derive(Debug, Default, Clone)]
+pub enum UpgradeSelection {
+    /// Prefer pinned versions from the existing lockfile, if possible.
+    #[default]
+    None,
+
+    /// Allow package upgrades for all packages, ignoring the existing lockfile.
+    All,
+
+    /// Allow package upgrades, but only for the specified packages.
+    Packages(Vec<Requirement>),
+}
+
+impl UpgradeSelection {
+    /// Determine the upgrade selection strategy from the command-line arguments.
+    pub fn from_args(upgrade: Option<bool>, upgrade_package: Vec<Requirement>) -> Option<Self> {
+        match upgrade {
+            Some(true) => Some(Self::All),
+            // TODO(charlie): `--no-upgrade` with `--upgrade-package` should allow the specified
+            // packages to be upgraded. Right now, `--upgrade-package` is silently ignored.
+            Some(false) => Some(Self::None),
+            None if upgrade_package.is_empty() => None,
+            None => Some(Self::Packages(upgrade_package)),
+        }
+    }
+
+    /// Combine a set of [`UpgradeSelection`] values.
+    #[must_use]
+    pub fn combine(self, other: Self) -> Self {
+        match self {
+            // Setting `--upgrade` or `--no-upgrade` should clear previous `--upgrade-package` selections.
+            Self::All | Self::None => self,
+            Self::Packages(self_packages) => match other {
+                // If `--upgrade` was enabled previously, `--upgrade-package` is subsumed by upgrading all packages.
+                Self::All => other,
+                // If `--no-upgrade` was enabled previously, then `--upgrade-package` enables an explicit upgrade of those packages.
+                Self::None => Self::Packages(self_packages),
+                // If `--upgrade-package` was included twice, combine the requirements.
+                Self::Packages(other_packages) => {
+                    let mut combined = self_packages;
+                    combined.extend(other_packages);
+                    Self::Packages(combined)
+                }
+            },
+        }
+    }
+}
+
 /// Whether to allow package upgrades.
-#[derive(Debug, Default, Clone, serde::Serialize, serde::Deserialize)]
-#[serde(rename_all = "kebab-case", deny_unknown_fields)]
+#[derive(Debug, Default, Clone)]
 pub enum Upgrade {
     /// Prefer pinned versions from the existing lockfile, if possible.
     #[default]
@@ -149,30 +197,28 @@ pub enum Upgrade {
     Packages(FxHashMap<PackageName, Vec<Requirement>>),
 }
 
-impl Upgrade {
-    /// Determine the [`Upgrade`] strategy from the command-line arguments.
-    pub fn from_args(upgrade: Option<bool>, upgrade_package: Vec<Requirement>) -> Self {
-        match upgrade {
-            Some(true) => Self::All,
-            Some(false) => Self::None,
-            None => {
-                if upgrade_package.is_empty() {
-                    Self::None
-                } else {
-                    Self::Packages(upgrade_package.into_iter().fold(
-                        FxHashMap::default(),
-                        |mut map, requirement| {
-                            map.entry(requirement.name.clone())
-                                .or_default()
-                                .push(requirement);
-                            map
-                        },
-                    ))
-                }
-            }
+/// Determine the [`Upgrade`] strategy from the command-line arguments.
+impl From<Option<UpgradeSelection>> for Upgrade {
+    fn from(value: Option<UpgradeSelection>) -> Self {
+        match value {
+            None => Self::None,
+            Some(UpgradeSelection::None) => Self::None,
+            Some(UpgradeSelection::All) => Self::All,
+            Some(UpgradeSelection::Packages(requirements)) => Self::Packages(
+                requirements
+                    .into_iter()
+                    .fold(FxHashMap::default(), |mut map, requirement| {
+                        map.entry(requirement.name.clone())
+                            .or_default()
+                            .push(requirement);
+                        map
+                    }),
+            ),
         }
     }
+}
 
+impl Upgrade {
     /// Create an [`Upgrade`] strategy to upgrade a single package.
     pub fn package(package_name: PackageName) -> Self {
         Self::Packages({
diff --git a/crates/uv-scripts/src/lib.rs b/crates/uv-scripts/src/lib.rs
index c70c2a354..0fac60d08 100644
--- a/crates/uv-scripts/src/lib.rs
+++ b/crates/uv-scripts/src/lib.rs
@@ -14,7 +14,7 @@ use uv_pep440::VersionSpecifiers;
 use uv_pep508::PackageName;
 use uv_pypi_types::VerbatimParsedUrl;
 use uv_redacted::DisplaySafeUrl;
-use uv_settings::{GlobalOptions, ResolverInstallerOptions};
+use uv_settings::{GlobalOptions, ResolverInstallerSchema};
 use uv_warnings::warn_user;
 use uv_workspace::pyproject::{ExtraBuildDependency, Sources};
 
@@ -424,7 +424,7 @@ pub struct ToolUv {
     #[serde(flatten)]
     pub globals: GlobalOptions,
     #[serde(flatten)]
-    pub top_level: ResolverInstallerOptions,
+    pub top_level: ResolverInstallerSchema,
     pub override_dependencies: Option<Vec<uv_pep508::Requirement<VerbatimParsedUrl>>>,
     pub constraint_dependencies: Option<Vec<uv_pep508::Requirement<VerbatimParsedUrl>>>,
     pub build_constraint_dependencies: Option<Vec<uv_pep508::Requirement<VerbatimParsedUrl>>>,
diff --git a/crates/uv-settings/src/combine.rs b/crates/uv-settings/src/combine.rs
index 3a297276f..02be876ec 100644
--- a/crates/uv-settings/src/combine.rs
+++ b/crates/uv-settings/src/combine.rs
@@ -5,7 +5,7 @@ use url::Url;
 
 use uv_configuration::{
     ExportFormat, IndexStrategy, KeyringProviderType, RequiredVersion, TargetTriple,
-    TrustedPublishing,
+    TrustedPublishing, UpgradeSelection,
 };
 use uv_distribution_types::{
     ConfigSettings, ExtraBuildVariables, Index, IndexUrl, PackageConfigSettings, PipExtraIndex,
@@ -181,6 +181,15 @@ impl Combine for Option<PackageConfigSettings> {
     }
 }
 
+impl Combine for Option<UpgradeSelection> {
+    fn combine(self, other: Self) -> Self {
+        match (self, other) {
+            (Some(a), Some(b)) => Some(a.combine(b)),
+            (a, b) => a.or(b),
+        }
+    }
+}
+
 impl Combine for serde::de::IgnoredAny {
     fn combine(self, _other: Self) -> Self {
         self
diff --git a/crates/uv-settings/src/lib.rs b/crates/uv-settings/src/lib.rs
index 4eda772ad..df15d60bf 100644
--- a/crates/uv-settings/src/lib.rs
+++ b/crates/uv-settings/src/lib.rs
@@ -301,7 +301,7 @@ fn warn_uv_toml_masked_fields(options: &Options) {
                 allow_insecure_host,
             },
         top_level:
-            ResolverInstallerOptions {
+            ResolverInstallerSchema {
                 index,
                 index_url,
                 extra_index_url,
diff --git a/crates/uv-settings/src/settings.rs b/crates/uv-settings/src/settings.rs
index 31218f2a5..96509f524 100644
--- a/crates/uv-settings/src/settings.rs
+++ b/crates/uv-settings/src/settings.rs
@@ -5,7 +5,7 @@ use serde::{Deserialize, Serialize};
 use uv_cache_info::CacheKey;
 use uv_configuration::{
     IndexStrategy, KeyringProviderType, PackageNameSpecifier, RequiredVersion, TargetTriple,
-    TrustedHost, TrustedPublishing,
+    TrustedHost, TrustedPublishing, UpgradeSelection,
 };
 use uv_distribution_types::{
     ConfigSettings, ExtraBuildVariables, Index, IndexUrl, IndexUrlError, PackageConfigSettings,
@@ -52,7 +52,7 @@ pub struct Options {
     pub globals: GlobalOptions,
 
     #[serde(flatten)]
-    pub top_level: ResolverInstallerOptions,
+    pub top_level: ResolverInstallerSchema,
 
     #[serde(flatten)]
     pub install_mirrors: PythonInstallMirrors,
@@ -161,7 +161,7 @@ pub struct Options {
 
 impl Options {
     /// Construct an [`Options`] with the given global and top-level settings.
-    pub fn simple(globals: GlobalOptions, top_level: ResolverInstallerOptions) -> Self {
+    pub fn simple(globals: GlobalOptions, top_level: ResolverInstallerSchema) -> Self {
         Self {
             globals,
             top_level,
@@ -369,8 +369,7 @@ pub struct ResolverOptions {
     pub config_settings_package: Option<PackageConfigSettings>,
     pub exclude_newer: ExcludeNewer,
     pub link_mode: Option<LinkMode>,
-    pub upgrade: Option<bool>,
-    pub upgrade_package: Option<Vec<Requirement<VerbatimParsedUrl>>>,
+    pub upgrade: Option<UpgradeSelection>,
     pub no_build: Option<bool>,
     pub no_build_package: Option<Vec<PackageName>>,
     pub no_binary: Option<bool>,
@@ -384,10 +383,159 @@ pub struct ResolverOptions {
 
 /// Shared settings, relevant to all operations that must resolve and install dependencies. The
 /// union of [`InstallerOptions`] and [`ResolverOptions`].
+#[derive(Debug, Clone, Default, CombineOptions)]
+pub struct ResolverInstallerOptions {
+    pub index: Option<Vec<Index>>,
+    pub index_url: Option<PipIndex>,
+    pub extra_index_url: Option<Vec<PipExtraIndex>>,
+    pub no_index: Option<bool>,
+    pub find_links: Option<Vec<PipFindLinks>>,
+    pub index_strategy: Option<IndexStrategy>,
+    pub keyring_provider: Option<KeyringProviderType>,
+    pub resolution: Option<ResolutionMode>,
+    pub prerelease: Option<PrereleaseMode>,
+    pub fork_strategy: Option<ForkStrategy>,
+    pub dependency_metadata: Option<Vec<StaticMetadata>>,
+    pub config_settings: Option<ConfigSettings>,
+    pub config_settings_package: Option<PackageConfigSettings>,
+    pub no_build_isolation: Option<bool>,
+    pub no_build_isolation_package: Option<Vec<PackageName>>,
+    pub extra_build_dependencies: Option<ExtraBuildDependencies>,
+    pub extra_build_variables: Option<ExtraBuildVariables>,
+    pub exclude_newer: Option<ExcludeNewerTimestamp>,
+    pub exclude_newer_package: Option<ExcludeNewerPackage>,
+    pub link_mode: Option<LinkMode>,
+    pub compile_bytecode: Option<bool>,
+    pub no_sources: Option<bool>,
+    pub upgrade: Option<UpgradeSelection>,
+    pub reinstall: Option<bool>,
+    pub reinstall_package: Option<Vec<PackageName>>,
+    pub no_build: Option<bool>,
+    pub no_build_package: Option<Vec<PackageName>>,
+    pub no_binary: Option<bool>,
+    pub no_binary_package: Option<Vec<PackageName>>,
+}
+
+impl From<ResolverInstallerSchema> for ResolverInstallerOptions {
+    fn from(value: ResolverInstallerSchema) -> Self {
+        let ResolverInstallerSchema {
+            index,
+            index_url,
+            extra_index_url,
+            no_index,
+            find_links,
+            index_strategy,
+            keyring_provider,
+            resolution,
+            prerelease,
+            fork_strategy,
+            dependency_metadata,
+            config_settings,
+            config_settings_package,
+            no_build_isolation,
+            no_build_isolation_package,
+            extra_build_dependencies,
+            extra_build_variables,
+            exclude_newer,
+            exclude_newer_package,
+            link_mode,
+            compile_bytecode,
+            no_sources,
+            upgrade,
+            upgrade_package,
+            reinstall,
+            reinstall_package,
+            no_build,
+            no_build_package,
+            no_binary,
+            no_binary_package,
+        } = value;
+        Self {
+            index,
+            index_url,
+            extra_index_url,
+            no_index,
+            find_links,
+            index_strategy,
+            keyring_provider,
+            resolution,
+            prerelease,
+            fork_strategy,
+            dependency_metadata,
+            config_settings,
+            config_settings_package,
+            no_build_isolation,
+            no_build_isolation_package,
+            extra_build_dependencies,
+            extra_build_variables,
+            exclude_newer,
+            exclude_newer_package,
+            link_mode,
+            compile_bytecode,
+            no_sources,
+            upgrade: UpgradeSelection::from_args(
+                upgrade,
+                upgrade_package
+                    .into_iter()
+                    .flatten()
+                    .map(Into::into)
+                    .collect(),
+            ),
+            reinstall,
+            reinstall_package,
+            no_build,
+            no_build_package,
+            no_binary,
+            no_binary_package,
+        }
+    }
+}
+
+impl ResolverInstallerSchema {
+    /// Resolve the [`ResolverInstallerSchema`] relative to the given root directory.
+    pub fn relative_to(self, root_dir: &Path) -> Result<Self, IndexUrlError> {
+        Ok(Self {
+            index: self
+                .index
+                .map(|index| {
+                    index
+                        .into_iter()
+                        .map(|index| index.relative_to(root_dir))
+                        .collect::<Result<Vec<_>, _>>()
+                })
+                .transpose()?,
+            index_url: self
+                .index_url
+                .map(|index_url| index_url.relative_to(root_dir))
+                .transpose()?,
+            extra_index_url: self
+                .extra_index_url
+                .map(|extra_index_url| {
+                    extra_index_url
+                        .into_iter()
+                        .map(|extra_index_url| extra_index_url.relative_to(root_dir))
+                        .collect::<Result<Vec<_>, _>>()
+                })
+                .transpose()?,
+            find_links: self
+                .find_links
+                .map(|find_links| {
+                    find_links
+                        .into_iter()
+                        .map(|find_link| find_link.relative_to(root_dir))
+                        .collect::<Result<Vec<_>, _>>()
+                })
+                .transpose()?,
+            ..self
+        })
+    }
+}
+
+/// The JSON schema for the `[tool.uv]` section of a `pyproject.toml` file.
 #[derive(Debug, Clone, Default, PartialEq, Eq, Deserialize, CombineOptions, OptionsMetadata)]
 #[serde(rename_all = "kebab-case")]
 #[cfg_attr(feature = "schemars", derive(schemars::JsonSchema))]
-pub struct ResolverInstallerOptions {
+pub struct ResolverInstallerSchema {
     /// The package indexes to use when resolving dependencies.
     ///
     /// Accepts either a repository compliant with [PEP 503](https://peps.python.org/pep-0503/)
@@ -814,46 +962,6 @@ pub struct ResolverInstallerOptions {
     pub no_binary_package: Option<Vec<PackageName>>,
 }
 
-impl ResolverInstallerOptions {
-    /// Resolve the [`ResolverInstallerOptions`] relative to the given root directory.
-    pub fn relative_to(self, root_dir: &Path) -> Result<Self, IndexUrlError> {
-        Ok(Self {
-            index: self
-                .index
-                .map(|index| {
-                    index
-                        .into_iter()
-                        .map(|index| index.relative_to(root_dir))
-                        .collect::<Result<Vec<_>, _>>()
-                })
-                .transpose()?,
-            index_url: self
-                .index_url
-                .map(|index_url| index_url.relative_to(root_dir))
-                .transpose()?,
-            extra_index_url: self
-                .extra_index_url
-                .map(|extra_index_url| {
-                    extra_index_url
-                        .into_iter()
-                        .map(|extra_index_url| extra_index_url.relative_to(root_dir))
-                        .collect::<Result<Vec<_>, _>>()
-                })
-                .transpose()?,
-            find_links: self
-                .find_links
-                .map(|find_links| {
-                    find_links
-                        .into_iter()
-                        .map(|find_link| find_link.relative_to(root_dir))
-                        .collect::<Result<Vec<_>, _>>()
-                })
-                .transpose()?,
-            ..self
-        })
-    }
-}
-
 /// Shared settings, relevant to all operations that might create managed python installations.
 #[derive(Debug, Clone, PartialEq, Eq, Deserialize, CombineOptions, OptionsMetadata)]
 #[serde(rename_all = "kebab-case")]
@@ -1752,8 +1860,8 @@ impl PipOptions {
     }
 }
 
-impl From<ResolverInstallerOptions> for ResolverOptions {
-    fn from(value: ResolverInstallerOptions) -> Self {
+impl From<ResolverInstallerSchema> for ResolverOptions {
+    fn from(value: ResolverInstallerSchema) -> Self {
         Self {
             index: value.index,
             index_url: value.index_url,
@@ -1778,8 +1886,15 @@ impl From<ResolverInstallerOptions> for ResolverOptions {
                     .collect(),
             ),
             link_mode: value.link_mode,
-            upgrade: value.upgrade,
-            upgrade_package: value.upgrade_package,
+            upgrade: UpgradeSelection::from_args(
+                value.upgrade,
+                value
+                    .upgrade_package
+                    .into_iter()
+                    .flatten()
+                    .map(Into::into)
+                    .collect(),
+            ),
             no_build: value.no_build,
             no_build_package: value.no_build_package,
             no_binary: value.no_binary,
@@ -1793,8 +1908,8 @@ impl From<ResolverInstallerOptions> for ResolverOptions {
     }
 }
 
-impl From<ResolverInstallerOptions> for InstallerOptions {
-    fn from(value: ResolverInstallerOptions) -> Self {
+impl From<ResolverInstallerSchema> for InstallerOptions {
+    fn from(value: ResolverInstallerSchema) -> Self {
         Self {
             index: value.index,
             index_url: value.index_url,
@@ -1830,7 +1945,7 @@ impl From<ResolverInstallerOptions> for InstallerOptions {
 
 /// The options persisted alongside an installed tool.
 ///
-/// A mirror of [`ResolverInstallerOptions`], without upgrades and reinstalls, which shouldn't be
+/// A mirror of [`ResolverInstallerSchema`], without upgrades and reinstalls, which shouldn't be
 /// persisted in a tool receipt.
 #[derive(
     Debug, Clone, Default, PartialEq, Eq, Serialize, Deserialize, CombineOptions, OptionsMetadata,
@@ -1925,7 +2040,6 @@ impl From<ToolOptions> for ResolverInstallerOptions {
             compile_bytecode: value.compile_bytecode,
             no_sources: value.no_sources,
             upgrade: None,
-            upgrade_package: None,
             reinstall: None,
             reinstall_package: None,
             no_build: value.no_build,
@@ -2120,7 +2234,7 @@ impl From<OptionsWire> for Options {
                 // Used twice for backwards compatibility
                 allow_insecure_host: allow_insecure_host.clone(),
             },
-            top_level: ResolverInstallerOptions {
+            top_level: ResolverInstallerSchema {
                 index,
                 index_url,
                 extra_index_url,
diff --git a/crates/uv/src/settings.rs b/crates/uv/src/settings.rs
index f56a02e82..27793c60d 100644
--- a/crates/uv/src/settings.rs
+++ b/crates/uv/src/settings.rs
@@ -24,7 +24,7 @@ use uv_configuration::{
     BuildOptions, Concurrency, DependencyGroups, DryRun, EditableMode, ExportFormat,
     ExtrasSpecification, HashCheckingMode, IndexStrategy, InstallOptions, KeyringProviderType,
     NoBinary, NoBuild, Preview, ProjectBuildBackend, Reinstall, RequiredVersion, SourceStrategy,
-    TargetTriple, TrustedHost, TrustedPublishing, Upgrade, VersionControlSystem,
+    TargetTriple, TrustedHost, TrustedPublishing, Upgrade, UpgradeSelection, VersionControlSystem,
 };
 use uv_distribution_types::{
     ConfigSettings, DependencyMetadata, ExtraBuildVariables, Index, IndexLocations, IndexUrl,
@@ -42,7 +42,7 @@ use uv_resolver::{
 };
 use uv_settings::{
     Combine, EnvironmentOptions, FilesystemOptions, Options, PipOptions, PublishOptions,
-    PythonInstallMirrors, ResolverInstallerOptions, ResolverOptions,
+    PythonInstallMirrors, ResolverInstallerOptions, ResolverInstallerSchema, ResolverOptions,
 };
 use uv_static::EnvVars;
 use uv_torch::TorchMode;
@@ -538,13 +538,14 @@ impl ToolRunSettings {
             }
         }
 
-        let options = resolver_installer_options(installer, build).combine(
-            filesystem
-                .clone()
-                .map(FilesystemOptions::into_options)
-                .map(|options| options.top_level)
-                .unwrap_or_default(),
-        );
+        let options =
+            resolver_installer_options(installer, build).combine(ResolverInstallerOptions::from(
+                filesystem
+                    .clone()
+                    .map(FilesystemOptions::into_options)
+                    .map(|options| options.top_level)
+                    .unwrap_or_default(),
+            ));
 
         let install_mirrors = filesystem
             .map(FilesystemOptions::into_options)
@@ -636,13 +637,14 @@ impl ToolInstallSettings {
             python,
         } = args;
 
-        let options = resolver_installer_options(installer, build).combine(
-            filesystem
-                .clone()
-                .map(FilesystemOptions::into_options)
-                .map(|options| options.top_level)
-                .unwrap_or_default(),
-        );
+        let options =
+            resolver_installer_options(installer, build).combine(ResolverInstallerOptions::from(
+                filesystem
+                    .clone()
+                    .map(FilesystemOptions::into_options)
+                    .map(|options| options.top_level)
+                    .unwrap_or_default(),
+            ));
 
         let install_mirrors = filesystem
             .map(FilesystemOptions::into_options)
@@ -777,9 +779,11 @@ impl ToolUpgradeSettings {
             .clone()
             .map(|options| options.install_mirrors)
             .unwrap_or_default();
-        let top_level = filesystem
-            .map(|options| options.top_level)
-            .unwrap_or_default();
+        let top_level = ResolverInstallerOptions::from(
+            filesystem
+                .map(|options| options.top_level)
+                .unwrap_or_default(),
+        );
 
         Self {
             names: if all { vec![] } else { name },
@@ -2798,6 +2802,8 @@ pub(crate) struct ResolverSettings {
 impl ResolverSettings {
     /// Resolve the [`ResolverSettings`] from the CLI and filesystem configuration.
     pub(crate) fn combine(args: ResolverOptions, filesystem: Option<FilesystemOptions>) -> Self {
+        // The problem is that for `upgrade`... we want to combine the two `Upgrade` structs,
+        // not the individual fields.
         let options = args.combine(ResolverOptions::from(
             filesystem
                 .map(FilesystemOptions::into_options)
@@ -2846,15 +2852,7 @@ impl From<ResolverOptions> for ResolverSettings {
             exclude_newer: value.exclude_newer,
             link_mode: value.link_mode.unwrap_or_default(),
             sources: SourceStrategy::from_args(value.no_sources.unwrap_or_default()),
-            upgrade: Upgrade::from_args(
-                value.upgrade,
-                value
-                    .upgrade_package
-                    .into_iter()
-                    .flatten()
-                    .map(Requirement::from)
-                    .collect(),
-            ),
+            upgrade: Upgrade::from(value.upgrade),
             build_options: BuildOptions::new(
                 NoBinary::from_args(value.no_binary, value.no_binary_package.unwrap_or_default()),
                 NoBuild::from_args(value.no_build, value.no_build_package.unwrap_or_default()),
@@ -2881,12 +2879,12 @@ impl ResolverInstallerSettings {
         args: ResolverInstallerOptions,
         filesystem: Option<FilesystemOptions>,
     ) -> Self {
-        let options = args.combine(
+        let options = args.combine(ResolverInstallerOptions::from(
             filesystem
                 .map(FilesystemOptions::into_options)
                 .map(|options| options.top_level)
                 .unwrap_or_default(),
-        );
+        ));
 
         Self::from(options)
     }
@@ -2945,15 +2943,7 @@ impl From<ResolverInstallerOptions> for ResolverInstallerSettings {
                 prerelease: value.prerelease.unwrap_or_default(),
                 resolution: value.resolution.unwrap_or_default(),
                 sources: SourceStrategy::from_args(value.no_sources.unwrap_or_default()),
-                upgrade: Upgrade::from_args(
-                    value.upgrade,
-                    value
-                        .upgrade_package
-                        .into_iter()
-                        .flatten()
-                        .map(Requirement::from)
-                        .collect(),
-                ),
+                upgrade: Upgrade::from(value.upgrade),
             },
             compile_bytecode: value.compile_bytecode.unwrap_or_default(),
             reinstall: Reinstall::from_args(
@@ -3098,7 +3088,7 @@ impl PipSettings {
             exclude_newer_package,
         } = pip.unwrap_or_default();
 
-        let ResolverInstallerOptions {
+        let ResolverInstallerSchema {
             index: top_level_index,
             index_url: top_level_index_url,
             extra_index_url: top_level_extra_index_url,
@@ -3327,14 +3317,23 @@ impl PipSettings {
                 args.no_sources.combine(no_sources).unwrap_or_default(),
             ),
             strict: args.strict.combine(strict).unwrap_or_default(),
-            upgrade: Upgrade::from_args(
-                args.upgrade.combine(upgrade),
-                args.upgrade_package
-                    .combine(upgrade_package)
-                    .into_iter()
-                    .flatten()
-                    .map(Requirement::from)
-                    .collect(),
+            upgrade: Upgrade::from(
+                UpgradeSelection::from_args(
+                    args.upgrade,
+                    args.upgrade_package
+                        .into_iter()
+                        .flatten()
+                        .map(Requirement::from)
+                        .collect(),
+                )
+                .combine(UpgradeSelection::from_args(
+                    upgrade,
+                    upgrade_package
+                        .into_iter()
+                        .flatten()
+                        .map(Requirement::from)
+                        .collect(),
+                )),
             ),
             reinstall: Reinstall::from_args(
                 args.reinstall.combine(reinstall),
@@ -3418,7 +3417,7 @@ impl PublishSettings {
             trusted_publishing,
             check_url,
         } = publish;
-        let ResolverInstallerOptions {
+        let ResolverInstallerSchema {
             keyring_provider,
             index,
             extra_index_url,
diff --git a/crates/uv/tests/it/show_settings.rs b/crates/uv/tests/it/show_settings.rs
index faae87628..c7018a6c6 100644
--- a/crates/uv/tests/it/show_settings.rs
+++ b/crates/uv/tests/it/show_settings.rs
@@ -3514,7 +3514,6 @@ fn resolve_tool() -> anyhow::Result<()> {
             compile_bytecode: None,
             no_sources: None,
             upgrade: None,
-            upgrade_package: None,
             reinstall: None,
             reinstall_package: None,
             no_build: None,
@@ -8569,7 +8568,6 @@ fn upgrade_pip_cli_config_interaction() -> anyhow::Result<()> {
     "})?;
 
     // Despite `upgrade = false` in the configuration file, we should mark `idna` for upgrade.
-    // TODO(charlie): This doesn't mark `idna` for upgrade; it just disables upgrades.
     uv_snapshot!(context.filters(), add_shared_args(context.pip_compile(), context.temp_dir.path())
         .arg("--upgrade-package")
         .arg("idna")
@@ -8727,7 +8725,30 @@ fn upgrade_pip_cli_config_interaction() -> anyhow::Result<()> {
             hash_checking: Some(
                 Verify,
             ),
-            upgrade: None,
+            upgrade: Packages(
+                {
+                    PackageName(
+                        "idna",
+                    ): [
+                        Requirement {
+                            name: PackageName(
+                                "idna",
+                            ),
+                            extras: [],
+                            groups: [],
+                            marker: true,
+                            source: Registry {
+                                specifier: VersionSpecifiers(
+                                    [],
+                                ),
+                                index: None,
+                                conflict: None,
+                            },
+                            origin: None,
+                        },
+                    ],
+                },
+            ),
             reinstall: None,
         },
     }
@@ -9600,7 +9621,6 @@ fn upgrade_project_cli_config_interaction() -> anyhow::Result<()> {
     "#})?;
 
     // Despite `upgrade = false` in the configuration file, we should mark `idna` for upgrade.
-    // TODO(charlie): This doesn't mark `idna` for upgrade; it just disables upgrades.
     uv_snapshot!(context.filters(), add_shared_args(context.lock(), context.temp_dir.path())
         .arg("--upgrade-package")
         .arg("idna")
@@ -9699,7 +9719,30 @@ fn upgrade_project_cli_config_interaction() -> anyhow::Result<()> {
             prerelease: IfNecessaryOrExplicit,
             resolution: Highest,
             sources: Enabled,
-            upgrade: None,
+            upgrade: Packages(
+                {
+                    PackageName(
+                        "idna",
+                    ): [
+                        Requirement {
+                            name: PackageName(
+                                "idna",
+                            ),
+                            extras: [],
+                            groups: [],
+                            marker: true,
+                            source: Registry {
+                                specifier: VersionSpecifiers(
+                                    [],
+                                ),
+                                index: None,
+                                conflict: None,
+                            },
+                            origin: None,
+                        },
+                    ],
+                },
+            ),
         },
     }