diff --git a/crates/uv-resolver/src/lib.rs b/crates/uv-resolver/src/lib.rs
index 7ede037f2e8c..950eb8a0ca43 100644
--- a/crates/uv-resolver/src/lib.rs
+++ b/crates/uv-resolver/src/lib.rs
@@ -12,9 +12,7 @@ pub use preferences::{Preference, PreferenceError, Preferences};
 pub use prerelease::PrereleaseMode;
 pub use pubgrub::{PubGrubSpecifier, PubGrubSpecifierError};
 pub use python_requirement::PythonRequirement;
-pub use requires_python::{
-    RequiresPython, RequiresPythonBound, RequiresPythonError, RequiresPythonRange,
-};
+pub use requires_python::{RequiresPython, RequiresPythonError, RequiresPythonRange};
 pub use resolution::{AnnotationStyle, DisplayResolutionGraph, ResolutionGraph};
 pub use resolution_mode::ResolutionMode;
 pub use resolver::{
diff --git a/crates/uv-resolver/src/lock/snapshots/uv_resolver__lock__tests__hash_optional_missing.snap b/crates/uv-resolver/src/lock/snapshots/uv_resolver__lock__tests__hash_optional_missing.snap
index e63cff079919..b4f8edfa3fa7 100644
--- a/crates/uv-resolver/src/lock/snapshots/uv_resolver__lock__tests__hash_optional_missing.snap
+++ b/crates/uv-resolver/src/lock/snapshots/uv_resolver__lock__tests__hash_optional_missing.snap
@@ -17,12 +17,12 @@ Ok(
                 ],
             ),
             range: RequiresPythonRange(
-                RequiresPythonBound(
+                LowerBound(
                     Included(
                         "3.12",
                     ),
                 ),
-                RequiresPythonBound(
+                UpperBound(
                     Unbounded,
                 ),
             ),
diff --git a/crates/uv-resolver/src/lock/snapshots/uv_resolver__lock__tests__hash_optional_present.snap b/crates/uv-resolver/src/lock/snapshots/uv_resolver__lock__tests__hash_optional_present.snap
index 4a9789a0b385..6fb234b37187 100644
--- a/crates/uv-resolver/src/lock/snapshots/uv_resolver__lock__tests__hash_optional_present.snap
+++ b/crates/uv-resolver/src/lock/snapshots/uv_resolver__lock__tests__hash_optional_present.snap
@@ -17,12 +17,12 @@ Ok(
                 ],
             ),
             range: RequiresPythonRange(
-                RequiresPythonBound(
+                LowerBound(
                     Included(
                         "3.12",
                     ),
                 ),
-                RequiresPythonBound(
+                UpperBound(
                     Unbounded,
                 ),
             ),
diff --git a/crates/uv-resolver/src/lock/snapshots/uv_resolver__lock__tests__hash_required_present.snap b/crates/uv-resolver/src/lock/snapshots/uv_resolver__lock__tests__hash_required_present.snap
index 04f906b20b65..742ce5519064 100644
--- a/crates/uv-resolver/src/lock/snapshots/uv_resolver__lock__tests__hash_required_present.snap
+++ b/crates/uv-resolver/src/lock/snapshots/uv_resolver__lock__tests__hash_required_present.snap
@@ -17,12 +17,12 @@ Ok(
                 ],
             ),
             range: RequiresPythonRange(
-                RequiresPythonBound(
+                LowerBound(
                     Included(
                         "3.12",
                     ),
                 ),
-                RequiresPythonBound(
+                UpperBound(
                     Unbounded,
                 ),
             ),
diff --git a/crates/uv-resolver/src/lock/snapshots/uv_resolver__lock__tests__missing_dependency_source_unambiguous.snap b/crates/uv-resolver/src/lock/snapshots/uv_resolver__lock__tests__missing_dependency_source_unambiguous.snap
index 3b1e8c307385..38cbef2bff9b 100644
--- a/crates/uv-resolver/src/lock/snapshots/uv_resolver__lock__tests__missing_dependency_source_unambiguous.snap
+++ b/crates/uv-resolver/src/lock/snapshots/uv_resolver__lock__tests__missing_dependency_source_unambiguous.snap
@@ -17,12 +17,12 @@ Ok(
                 ],
             ),
             range: RequiresPythonRange(
-                RequiresPythonBound(
+                LowerBound(
                     Included(
                         "3.12",
                     ),
                 ),
-                RequiresPythonBound(
+                UpperBound(
                     Unbounded,
                 ),
             ),
diff --git a/crates/uv-resolver/src/lock/snapshots/uv_resolver__lock__tests__missing_dependency_source_version_unambiguous.snap b/crates/uv-resolver/src/lock/snapshots/uv_resolver__lock__tests__missing_dependency_source_version_unambiguous.snap
index 3b1e8c307385..38cbef2bff9b 100644
--- a/crates/uv-resolver/src/lock/snapshots/uv_resolver__lock__tests__missing_dependency_source_version_unambiguous.snap
+++ b/crates/uv-resolver/src/lock/snapshots/uv_resolver__lock__tests__missing_dependency_source_version_unambiguous.snap
@@ -17,12 +17,12 @@ Ok(
                 ],
             ),
             range: RequiresPythonRange(
-                RequiresPythonBound(
+                LowerBound(
                     Included(
                         "3.12",
                     ),
                 ),
-                RequiresPythonBound(
+                UpperBound(
                     Unbounded,
                 ),
             ),
diff --git a/crates/uv-resolver/src/lock/snapshots/uv_resolver__lock__tests__missing_dependency_version_unambiguous.snap b/crates/uv-resolver/src/lock/snapshots/uv_resolver__lock__tests__missing_dependency_version_unambiguous.snap
index 3b1e8c307385..38cbef2bff9b 100644
--- a/crates/uv-resolver/src/lock/snapshots/uv_resolver__lock__tests__missing_dependency_version_unambiguous.snap
+++ b/crates/uv-resolver/src/lock/snapshots/uv_resolver__lock__tests__missing_dependency_version_unambiguous.snap
@@ -17,12 +17,12 @@ Ok(
                 ],
             ),
             range: RequiresPythonRange(
-                RequiresPythonBound(
+                LowerBound(
                     Included(
                         "3.12",
                     ),
                 ),
-                RequiresPythonBound(
+                UpperBound(
                     Unbounded,
                 ),
             ),
diff --git a/crates/uv-resolver/src/lock/snapshots/uv_resolver__lock__tests__source_direct_has_subdir.snap b/crates/uv-resolver/src/lock/snapshots/uv_resolver__lock__tests__source_direct_has_subdir.snap
index 640ec123cd5f..554ec8622ff5 100644
--- a/crates/uv-resolver/src/lock/snapshots/uv_resolver__lock__tests__source_direct_has_subdir.snap
+++ b/crates/uv-resolver/src/lock/snapshots/uv_resolver__lock__tests__source_direct_has_subdir.snap
@@ -17,12 +17,12 @@ Ok(
                 ],
             ),
             range: RequiresPythonRange(
-                RequiresPythonBound(
+                LowerBound(
                     Included(
                         "3.12",
                     ),
                 ),
-                RequiresPythonBound(
+                UpperBound(
                     Unbounded,
                 ),
             ),
diff --git a/crates/uv-resolver/src/lock/snapshots/uv_resolver__lock__tests__source_direct_no_subdir.snap b/crates/uv-resolver/src/lock/snapshots/uv_resolver__lock__tests__source_direct_no_subdir.snap
index 278825029ba1..df511a98dffe 100644
--- a/crates/uv-resolver/src/lock/snapshots/uv_resolver__lock__tests__source_direct_no_subdir.snap
+++ b/crates/uv-resolver/src/lock/snapshots/uv_resolver__lock__tests__source_direct_no_subdir.snap
@@ -17,12 +17,12 @@ Ok(
                 ],
             ),
             range: RequiresPythonRange(
-                RequiresPythonBound(
+                LowerBound(
                     Included(
                         "3.12",
                     ),
                 ),
-                RequiresPythonBound(
+                UpperBound(
                     Unbounded,
                 ),
             ),
diff --git a/crates/uv-resolver/src/lock/snapshots/uv_resolver__lock__tests__source_directory.snap b/crates/uv-resolver/src/lock/snapshots/uv_resolver__lock__tests__source_directory.snap
index b40e3bf2164a..60b749cac557 100644
--- a/crates/uv-resolver/src/lock/snapshots/uv_resolver__lock__tests__source_directory.snap
+++ b/crates/uv-resolver/src/lock/snapshots/uv_resolver__lock__tests__source_directory.snap
@@ -17,12 +17,12 @@ Ok(
                 ],
             ),
             range: RequiresPythonRange(
-                RequiresPythonBound(
+                LowerBound(
                     Included(
                         "3.12",
                     ),
                 ),
-                RequiresPythonBound(
+                UpperBound(
                     Unbounded,
                 ),
             ),
diff --git a/crates/uv-resolver/src/lock/snapshots/uv_resolver__lock__tests__source_editable.snap b/crates/uv-resolver/src/lock/snapshots/uv_resolver__lock__tests__source_editable.snap
index fa6e8aa2194d..f90a8f7c4a99 100644
--- a/crates/uv-resolver/src/lock/snapshots/uv_resolver__lock__tests__source_editable.snap
+++ b/crates/uv-resolver/src/lock/snapshots/uv_resolver__lock__tests__source_editable.snap
@@ -17,12 +17,12 @@ Ok(
                 ],
             ),
             range: RequiresPythonRange(
-                RequiresPythonBound(
+                LowerBound(
                     Included(
                         "3.12",
                     ),
                 ),
-                RequiresPythonBound(
+                UpperBound(
                     Unbounded,
                 ),
             ),
diff --git a/crates/uv-resolver/src/marker.rs b/crates/uv-resolver/src/marker.rs
index 5e9252260159..944362c1e4b7 100644
--- a/crates/uv-resolver/src/marker.rs
+++ b/crates/uv-resolver/src/marker.rs
@@ -1,5 +1,4 @@
-use crate::requires_python::RequiresPythonRange;
-use crate::RequiresPythonBound;
+use crate::requires_python::{LowerBound, RequiresPythonRange, UpperBound};
 use pep440_rs::Version;
 use pep508_rs::{MarkerTree, MarkerTreeKind, MarkerValueVersion};
 use pubgrub::Range;
@@ -62,7 +61,7 @@ pub(crate) fn requires_python(tree: &MarkerTree) -> Option<RequiresPythonRange>
     let (lower, upper) = range.bounding_range()?;
 
     Some(RequiresPythonRange::new(
-        RequiresPythonBound::new(lower.cloned()),
-        RequiresPythonBound::new(upper.cloned()),
+        LowerBound::new(lower.cloned()),
+        UpperBound::new(upper.cloned()),
     ))
 }
diff --git a/crates/uv-resolver/src/requires_python.rs b/crates/uv-resolver/src/requires_python.rs
index 9d70acd68acc..f433832b669b 100644
--- a/crates/uv-resolver/src/requires_python.rs
+++ b/crates/uv-resolver/src/requires_python.rs
@@ -45,8 +45,8 @@ impl RequiresPython {
                 version.clone(),
             )),
             range: RequiresPythonRange(
-                RequiresPythonBound::new(Bound::Included(version.clone())),
-                RequiresPythonBound::new(Bound::Unbounded),
+                LowerBound::new(Bound::Included(version.clone())),
+                UpperBound::new(Bound::Unbounded),
             ),
         }
     }
@@ -60,10 +60,7 @@ impl RequiresPython {
                 .unwrap_or((Bound::Unbounded, Bound::Unbounded));
         Ok(Self {
             specifiers: specifiers.clone(),
-            range: RequiresPythonRange(
-                RequiresPythonBound(lower_bound),
-                RequiresPythonBound(upper_bound),
-            ),
+            range: RequiresPythonRange(LowerBound(lower_bound), UpperBound(upper_bound)),
         })
     }
 
@@ -103,10 +100,7 @@ impl RequiresPython {
 
         Ok(Some(Self {
             specifiers,
-            range: RequiresPythonRange(
-                RequiresPythonBound(lower_bound),
-                RequiresPythonBound(upper_bound),
-            ),
+            range: RequiresPythonRange(LowerBound(lower_bound), UpperBound(upper_bound)),
         }))
     }
 
@@ -273,19 +267,19 @@ impl RequiresPython {
     }
 
     /// Returns the [`RequiresPythonBound`] truncated to the major and minor version.
-    pub fn bound_major_minor(&self) -> RequiresPythonBound {
+    pub fn bound_major_minor(&self) -> LowerBound {
         match self.range.lower().as_ref() {
             // Ex) `>=3.10.1` -> `>=3.10`
-            Bound::Included(version) => RequiresPythonBound(Bound::Included(Version::new(
+            Bound::Included(version) => LowerBound(Bound::Included(Version::new(
                 version.release().iter().take(2),
             ))),
             // Ex) `>3.10.1` -> `>=3.10`
             // This is unintuitive, but `>3.10.1` does indicate that _some_ version of Python 3.10
             // is supported.
-            Bound::Excluded(version) => RequiresPythonBound(Bound::Included(Version::new(
+            Bound::Excluded(version) => LowerBound(Bound::Included(Version::new(
                 version.release().iter().take(2),
             ))),
-            Bound::Unbounded => RequiresPythonBound(Bound::Unbounded),
+            Bound::Unbounded => LowerBound(Bound::Unbounded),
         }
     }
 
@@ -387,8 +381,7 @@ impl RequiresPython {
                     };
 
                     // Ex) If the wheel bound is `3.6`, then it doesn't match `>=3.10`.
-                    let wheel_bound =
-                        RequiresPythonBound(Bound::Included(Version::new([3, minor])));
+                    let wheel_bound = LowerBound(Bound::Included(Version::new([3, minor])));
                     wheel_bound >= self.bound_major_minor()
                 })
             } else if abi_tag.starts_with("cp2") || abi_tag.starts_with("pypy2") {
@@ -402,7 +395,7 @@ impl RequiresPython {
                     return true;
                 };
 
-                let wheel_bound = RequiresPythonBound(Bound::Included(Version::new([3, minor])));
+                let wheel_bound = LowerBound(Bound::Included(Version::new([3, minor])));
                 wheel_bound >= self.bound_major_minor()
             } else if let Some(minor_no_dot_abi) = abi_tag.strip_prefix("pypy3") {
                 // Given  `pypy39_pp73`, we just removed `pypy3`, now we remove `_pp73` ...
@@ -416,7 +409,7 @@ impl RequiresPython {
                     return true;
                 };
 
-                let wheel_bound = RequiresPythonBound(Bound::Included(Version::new([3, minor])));
+                let wheel_bound = LowerBound(Bound::Included(Version::new([3, minor])));
                 wheel_bound >= self.bound_major_minor()
             } else {
                 // Unknown python tag -> allowed.
@@ -449,40 +442,34 @@ impl<'de> serde::Deserialize<'de> for RequiresPython {
                 .unwrap_or((Bound::Unbounded, Bound::Unbounded));
         Ok(Self {
             specifiers,
-            range: RequiresPythonRange(
-                RequiresPythonBound(lower_bound),
-                RequiresPythonBound(upper_bound),
-            ),
+            range: RequiresPythonRange(LowerBound(lower_bound), UpperBound(upper_bound)),
         })
     }
 }
 
 #[derive(Debug, Clone, Eq, PartialEq, Hash)]
-pub struct RequiresPythonRange(RequiresPythonBound, RequiresPythonBound);
+pub struct RequiresPythonRange(LowerBound, UpperBound);
 
 impl RequiresPythonRange {
     /// Initialize a [`RequiresPythonRange`] with the given bounds.
-    pub fn new(lower: RequiresPythonBound, upper: RequiresPythonBound) -> Self {
+    pub fn new(lower: LowerBound, upper: UpperBound) -> Self {
         Self(lower, upper)
     }
 
     /// Returns the lower bound.
-    pub fn lower(&self) -> &RequiresPythonBound {
+    pub fn lower(&self) -> &LowerBound {
         &self.0
     }
 
     /// Returns the upper bound.
-    pub fn upper(&self) -> &RequiresPythonBound {
+    pub fn upper(&self) -> &UpperBound {
         &self.1
     }
 }
 
 impl Default for RequiresPythonRange {
     fn default() -> Self {
-        Self(
-            RequiresPythonBound(Bound::Unbounded),
-            RequiresPythonBound(Bound::Unbounded),
-        )
+        Self(LowerBound(Bound::Unbounded), UpperBound(Bound::Unbounded))
     }
 }
 
@@ -495,17 +482,117 @@ impl From<RequiresPythonRange> for Range<Version> {
     }
 }
 
+/// A simplified marker is just like a normal marker, except it has possibly
+/// been simplified by `requires-python`.
+///
+/// A simplified marker should only exist in contexts where a `requires-python`
+/// setting can be assumed. In order to get a "normal" marker out of
+/// a simplified marker, one must re-contextualize it by adding the
+/// `requires-python` constraint back to the marker.
+#[derive(Clone, Debug, Default, Eq, PartialEq, PartialOrd, Ord, serde::Deserialize)]
+pub(crate) struct SimplifiedMarkerTree(MarkerTree);
+
+impl SimplifiedMarkerTree {
+    /// Simplifies the given markers by assuming the given `requires-python`
+    /// bound is true.
+    pub(crate) fn new(
+        requires_python: &RequiresPython,
+        marker: MarkerTree,
+    ) -> SimplifiedMarkerTree {
+        SimplifiedMarkerTree(requires_python.simplify_markers(marker))
+    }
+
+    /// Complexifies the given markers by adding the given `requires-python` as
+    /// a constraint to these simplified markers.
+    pub(crate) fn into_marker(self, requires_python: &RequiresPython) -> MarkerTree {
+        requires_python.complexify_markers(self.0)
+    }
+
+    /// Attempts to convert this simplified marker to a string.
+    ///
+    /// This only returns `None` when the underlying marker is always true,
+    /// i.e., it matches all possible marker environments.
+    pub(crate) fn try_to_string(&self) -> Option<String> {
+        self.0.try_to_string()
+    }
+
+    /// Returns the underlying marker tree without re-complexifying them.
+    pub(crate) fn as_simplified_marker_tree(&self) -> &MarkerTree {
+        &self.0
+    }
+}
+
 #[derive(Debug, Clone, Eq, PartialEq, Hash)]
-pub struct RequiresPythonBound(Bound<Version>);
+pub struct LowerBound(Bound<Version>);
 
-impl Default for RequiresPythonBound {
+impl PartialOrd for LowerBound {
+    fn partial_cmp(&self, other: &Self) -> Option<Ordering> {
+        Some(self.cmp(other))
+    }
+}
+
+/// See: <https://github.com/pubgrub-rs/pubgrub/blob/4b4b44481c5f93f3233221dc736dd23e67e00992/src/range.rs#L324>
+impl Ord for LowerBound {
+    fn cmp(&self, other: &Self) -> Ordering {
+        let left = self.0.as_ref();
+        let right = other.0.as_ref();
+
+        match (left, right) {
+            // left:   ∞-----
+            // right:  ∞-----
+            (Bound::Unbounded, Bound::Unbounded) => Ordering::Equal,
+            // left:     [---
+            // right:  ∞-----
+            (Bound::Included(_left), Bound::Unbounded) => Ordering::Greater,
+            // left:     ]---
+            // right:  ∞-----
+            (Bound::Excluded(_left), Bound::Unbounded) => Ordering::Greater,
+            // left:   ∞-----
+            // right:    [---
+            (Bound::Unbounded, Bound::Included(_right)) => Ordering::Less,
+            // left:   [----- OR [----- OR   [-----
+            // right:    [--- OR [----- OR [---
+            (Bound::Included(left), Bound::Included(right)) => left.cmp(right),
+            (Bound::Excluded(left), Bound::Included(right)) => match left.cmp(right) {
+                // left:   ]-----
+                // right:    [---
+                Ordering::Less => Ordering::Less,
+                // left:   ]-----
+                // right:  [---
+                Ordering::Equal => Ordering::Greater,
+                // left:     ]---
+                // right:  [-----
+                Ordering::Greater => Ordering::Greater,
+            },
+            // left:   ∞-----
+            // right:    ]---
+            (Bound::Unbounded, Bound::Excluded(_right)) => Ordering::Less,
+            (Bound::Included(left), Bound::Excluded(right)) => match left.cmp(right) {
+                // left:   [-----
+                // right:    ]---
+                Ordering::Less => Ordering::Less,
+                // left:   [-----
+                // right:  ]---
+                Ordering::Equal => Ordering::Less,
+                // left:     [---
+                // right:  ]-----
+                Ordering::Greater => Ordering::Greater,
+            },
+            // left:   ]----- OR ]----- OR   ]---
+            // right:    ]--- OR ]----- OR ]-----
+            (Bound::Excluded(left), Bound::Excluded(right)) => left.cmp(right),
+        }
+    }
+}
+
+impl Default for LowerBound {
     fn default() -> Self {
         Self(Bound::Unbounded)
     }
 }
 
-impl RequiresPythonBound {
-    /// Initialize a [`RequiresPythonBound`] with the given bound.
+impl LowerBound {
+    /// Initialize a [`LowerBound`] with the given bound.
     ///
     /// These bounds use release-only semantics when comparing versions.
     pub fn new(bound: Bound<Version>) -> Self {
@@ -517,7 +604,7 @@ impl RequiresPythonBound {
     }
 }
 
-impl Deref for RequiresPythonBound {
+impl Deref for LowerBound {
     type Target = Bound<Version>;
 
     fn deref(&self) -> &Self::Target {
@@ -525,72 +612,106 @@ impl Deref for RequiresPythonBound {
     }
 }
 
-impl From<RequiresPythonBound> for Bound<Version> {
-    fn from(bound: RequiresPythonBound) -> Self {
+impl From<LowerBound> for Bound<Version> {
+    fn from(bound: LowerBound) -> Self {
         bound.0
     }
 }
 
-impl PartialOrd for RequiresPythonBound {
+#[derive(Debug, Clone, Eq, PartialEq, Hash)]
+pub struct UpperBound(Bound<Version>);
+
+impl PartialOrd for UpperBound {
     fn partial_cmp(&self, other: &Self) -> Option<Ordering> {
         Some(self.cmp(other))
     }
 }
 
-impl Ord for RequiresPythonBound {
+/// See: <https://github.com/pubgrub-rs/pubgrub/blob/4b4b44481c5f93f3233221dc736dd23e67e00992/src/range.rs#L324>
+impl Ord for UpperBound {
     fn cmp(&self, other: &Self) -> Ordering {
-        match (self.as_ref(), other.as_ref()) {
-            (Bound::Included(a), Bound::Included(b)) => a.cmp(b),
-            (Bound::Included(a), Bound::Excluded(b)) => a.cmp(b).then(Ordering::Less),
-            (Bound::Excluded(a), Bound::Included(b)) => a.cmp(b).then(Ordering::Greater),
-            (Bound::Excluded(a), Bound::Excluded(b)) => a.cmp(b),
+        let left = self.0.as_ref();
+        let right = other.0.as_ref();
+
+        match (left, right) {
+            // left:   -----∞
+            // right:  -----∞
             (Bound::Unbounded, Bound::Unbounded) => Ordering::Equal,
-            (Bound::Unbounded, _) => Ordering::Less,
-            (_, Bound::Unbounded) => Ordering::Greater,
+            // left:   ---]
+            // right:  -----∞
+            (Bound::Included(_left), Bound::Unbounded) => Ordering::Less,
+            // left:   ---[
+            // right:  -----∞
+            (Bound::Excluded(_left), Bound::Unbounded) => Ordering::Less,
+            // left:  -----∞
+            // right: ---]
+            (Bound::Unbounded, Bound::Included(_right)) => Ordering::Greater,
+            // left:   -----] OR -----] OR ---]
+            // right:    ---] OR -----] OR -----]
+            (Bound::Included(left), Bound::Included(right)) => left.cmp(right),
+            (Bound::Excluded(left), Bound::Included(right)) => match left.cmp(right) {
+                // left:   ---[
+                // right:  -----]
+                Ordering::Less => Ordering::Less,
+                // left:   -----[
+                // right:  -----]
+                Ordering::Equal => Ordering::Less,
+                // left:   -----[
+                // right:  ---]
+                Ordering::Greater => Ordering::Greater,
+            },
+            (Bound::Unbounded, Bound::Excluded(_right)) => Ordering::Greater,
+            (Bound::Included(left), Bound::Excluded(right)) => match left.cmp(right) {
+                // left:   ---]
+                // right:  -----[
+                Ordering::Less => Ordering::Less,
+                // left:   -----]
+                // right:  -----[
+                Ordering::Equal => Ordering::Greater,
+                // left:   -----]
+                // right:  ---[
+                Ordering::Greater => Ordering::Greater,
+            },
+            // left:   -----[ OR -----[ OR ---[
+            // right:  ---[   OR -----[ OR -----[
+            (Bound::Excluded(left), Bound::Excluded(right)) => left.cmp(right),
         }
     }
 }
 
-/// A simplified marker is just like a normal marker, except it has possibly
-/// been simplified by `requires-python`.
-///
-/// A simplified marker should only exist in contexts where a `requires-python`
-/// setting can be assumed. In order to get a "normal" marker out of
-/// a simplified marker, one must re-contextualize it by adding the
-/// `requires-python` constraint back to the marker.
-#[derive(Clone, Debug, Default, Eq, PartialEq, PartialOrd, Ord, serde::Deserialize)]
-pub(crate) struct SimplifiedMarkerTree(MarkerTree);
-
-impl SimplifiedMarkerTree {
-    /// Simplifies the given markers by assuming the given `requires-python`
-    /// bound is true.
-    pub(crate) fn new(
-        requires_python: &RequiresPython,
-        marker: MarkerTree,
-    ) -> SimplifiedMarkerTree {
-        SimplifiedMarkerTree(requires_python.simplify_markers(marker))
-    }
-
-    /// Complexifies the given markers by adding the given `requires-python` as
-    /// a constraint to these simplified markers.
-    pub(crate) fn into_marker(self, requires_python: &RequiresPython) -> MarkerTree {
-        requires_python.complexify_markers(self.0)
+impl Default for UpperBound {
+    fn default() -> Self {
+        Self(Bound::Unbounded)
     }
+}
 
-    /// Attempts to convert this simplified marker to a string.
+impl UpperBound {
+    /// Initialize a [`UpperBound`] with the given bound.
     ///
-    /// This only returns `None` when the underlying marker is always true,
-    /// i.e., it matches all possible marker environments.
-    pub(crate) fn try_to_string(&self) -> Option<String> {
-        self.0.try_to_string()
+    /// These bounds use release-only semantics when comparing versions.
+    pub fn new(bound: Bound<Version>) -> Self {
+        Self(match bound {
+            Bound::Included(version) => Bound::Included(version.only_release()),
+            Bound::Excluded(version) => Bound::Excluded(version.only_release()),
+            Bound::Unbounded => Bound::Unbounded,
+        })
     }
+}
 
-    /// Returns the underlying marker tree without re-complexifying them.
-    pub(crate) fn as_simplified_marker_tree(&self) -> &MarkerTree {
+impl Deref for UpperBound {
+    type Target = Bound<Version>;
+
+    fn deref(&self) -> &Self::Target {
         &self.0
     }
 }
 
+impl From<UpperBound> for Bound<Version> {
+    fn from(bound: UpperBound) -> Self {
+        bound.0
+    }
+}
+
 #[cfg(test)]
 mod tests {
     use std::cmp::Ordering;
@@ -600,7 +721,8 @@ mod tests {
     use distribution_filename::WheelFilename;
     use pep440_rs::{Version, VersionSpecifiers};
 
-    use crate::{RequiresPython, RequiresPythonBound};
+    use crate::requires_python::{LowerBound, UpperBound};
+    use crate::RequiresPython;
 
     #[test]
     fn requires_python_included() {
@@ -663,18 +785,39 @@ mod tests {
     }
 
     #[test]
-    fn ordering() {
+    fn lower_bound_ordering() {
         let versions = &[
             // No bound
-            RequiresPythonBound::new(Bound::Unbounded),
+            LowerBound::new(Bound::Unbounded),
             // >=3.8
-            RequiresPythonBound::new(Bound::Included(Version::new([3, 8]))),
+            LowerBound::new(Bound::Included(Version::new([3, 8]))),
             // >3.8
-            RequiresPythonBound::new(Bound::Excluded(Version::new([3, 8]))),
+            LowerBound::new(Bound::Excluded(Version::new([3, 8]))),
             // >=3.8.1
-            RequiresPythonBound::new(Bound::Included(Version::new([3, 8, 1]))),
+            LowerBound::new(Bound::Included(Version::new([3, 8, 1]))),
             // >3.8.1
-            RequiresPythonBound::new(Bound::Excluded(Version::new([3, 8, 1]))),
+            LowerBound::new(Bound::Excluded(Version::new([3, 8, 1]))),
+        ];
+        for (i, v1) in versions.iter().enumerate() {
+            for v2 in &versions[i + 1..] {
+                assert_eq!(v1.cmp(v2), Ordering::Less, "less: {v1:?}\ngreater: {v2:?}");
+            }
+        }
+    }
+
+    #[test]
+    fn upper_bound_ordering() {
+        let versions = &[
+            // <3.8
+            UpperBound::new(Bound::Excluded(Version::new([3, 8]))),
+            // <=3.8
+            UpperBound::new(Bound::Included(Version::new([3, 8]))),
+            // <3.8.1
+            UpperBound::new(Bound::Excluded(Version::new([3, 8, 1]))),
+            // <=3.8.1
+            UpperBound::new(Bound::Included(Version::new([3, 8, 1]))),
+            // No bound
+            UpperBound::new(Bound::Unbounded),
         ];
         for (i, v1) in versions.iter().enumerate() {
             for v2 in &versions[i + 1..] {
diff --git a/crates/uv/tests/lock.rs b/crates/uv/tests/lock.rs
index f896010165ee..e8d448d509c9 100644
--- a/crates/uv/tests/lock.rs
+++ b/crates/uv/tests/lock.rs
@@ -12120,3 +12120,375 @@ fn lock_split_python_environment() -> Result<()> {
 
     Ok(())
 }
+
+/// Correctly narrow the Python requirement when upper bounds are present.
+///
+/// See: <https://github.com/astral-sh/uv/issues/6911>
+#[test]
+fn lock_python_upper_bound() -> Result<()> {
+    let context = TestContext::new("3.12");
+
+    let pyproject_toml = context.temp_dir.child("pyproject.toml");
+    pyproject_toml.write_str(
+        r#"
+        [project]
+        name = "project"
+        version = "0.1.0"
+        requires-python = ">=3.8"
+        dependencies = ["magika; python_version < '3.13'"]
+
+        [build-system]
+        requires = ["setuptools>=42"]
+        build-backend = "setuptools.build_meta"
+        "#,
+    )?;
+
+    uv_snapshot!(context.filters(), context.lock(), @r###"
+    success: true
+    exit_code: 0
+    ----- stdout -----
+
+    ----- stderr -----
+    Resolved 18 packages in [TIME]
+    "###);
+
+    let lock = fs_err::read_to_string(context.temp_dir.join("uv.lock")).unwrap();
+
+    insta::with_settings!({
+        filters => context.filters(),
+    }, {
+        assert_snapshot!(
+            lock, @r###"
+        version = 1
+        requires-python = ">=3.8"
+        resolution-markers = [
+            "python_full_version >= '3.13'",
+            "python_full_version < '3.9'",
+            "python_full_version >= '3.9' and python_full_version < '3.13'",
+        ]
+
+        [options]
+        exclude-newer = "2024-03-25T00:00:00Z"
+
+        [[package]]
+        name = "click"
+        version = "8.1.7"
+        source = { registry = "https://pypi.org/simple" }
+        dependencies = [
+            { name = "colorama", marker = "platform_system == 'Windows'" },
+        ]
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+        ]
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+        [[package]]
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+        version = "0.4.6"
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+        dependencies = [
+            { name = "colorama", marker = "platform_system == 'Windows'" },
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+        sdist = { url = "https://files.pythonhosted.org/packages/ea/85/3ce0f9f7d3f596e7ea57f4e5ce8c18cb44e4a9daa58ddb46ee0d13d6bff8/tqdm-4.66.2.tar.gz", hash = "sha256:6cd52cdf0fef0e0f543299cfc96fec90d7b8a7e88745f411ec33eb44d5ed3531", size = 169462 }
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+        ]
+        "###
+        );
+    });
+
+    // Re-run with `--locked`.
+    uv_snapshot!(context.filters(), context.lock().arg("--locked"), @r###"
+    success: true
+    exit_code: 0
+    ----- stdout -----
+
+    ----- stderr -----
+    Resolved 18 packages in [TIME]
+    "###);
+
+    // Re-run with `--offline`. We shouldn't need a network connection to validate an
+    // already-correct lockfile with immutable metadata.
+    uv_snapshot!(context.filters(), context.lock().arg("--locked").arg("--offline").arg("--no-cache"), @r###"
+    success: true
+    exit_code: 0
+    ----- stdout -----
+
+    ----- stderr -----
+    Resolved 18 packages in [TIME]
+    "###);
+
+    Ok(())
+}
diff --git a/crates/uv/tests/pip_compile.rs b/crates/uv/tests/pip_compile.rs
index edafa06068ef..98e9fa9eddb8 100644
--- a/crates/uv/tests/pip_compile.rs
+++ b/crates/uv/tests/pip_compile.rs
@@ -12315,9 +12315,9 @@ fn importlib_metadata_not_repeated() -> Result<()> {
         # via -r requirements.in
     colorama==0.4.6 ; os_name == 'nt'
         # via build
-    importlib-metadata==6.7.0 ; python_full_version < '3.10'
+    importlib-metadata==6.7.0 ; python_full_version < '3.8'
         # via build
-    importlib-metadata==7.1.0 ; python_full_version >= '3.10' and python_full_version < '3.10.2'
+    importlib-metadata==7.1.0 ; python_full_version >= '3.8' and python_full_version < '3.10.2'
         # via build
     packaging==24.0
         # via build
@@ -12329,9 +12329,9 @@ fn importlib_metadata_not_repeated() -> Result<()> {
         #   pyproject-hooks
     typing-extensions==4.7.1 ; python_full_version < '3.8'
         # via importlib-metadata
-    zipp==3.15.0 ; python_full_version < '3.10'
+    zipp==3.15.0 ; python_full_version < '3.8'
         # via importlib-metadata
-    zipp==3.18.1 ; python_full_version >= '3.10' and python_full_version < '3.10.2'
+    zipp==3.18.1 ; python_full_version >= '3.8' and python_full_version < '3.10.2'
         # via importlib-metadata
 
     ----- stderr -----