diff --git a/crates/uv-workspace/src/pyproject_mut.rs b/crates/uv-workspace/src/pyproject_mut.rs
index 35c66550f..25544cc05 100644
--- a/crates/uv-workspace/src/pyproject_mut.rs
+++ b/crates/uv-workspace/src/pyproject_mut.rs
@@ -1,3 +1,4 @@
+use std::cmp::Ordering;
 use std::path::Path;
 use std::str::FromStr;
 use std::{fmt, mem};
@@ -918,14 +919,35 @@ pub fn add_dependency(
         [] => {
             #[derive(Debug, Copy, Clone)]
             enum Sort {
-                /// The list is sorted in a case-sensitive manner.
-                CaseSensitive,
                 /// The list is sorted in a case-insensitive manner.
                 CaseInsensitive,
+                /// The list is sorted in a case-sensitive manner.
+                CaseSensitive,
                 /// The list is unsorted.
                 Unsorted,
             }
 
+            /// Compare two [`Value`] requirements case-insensitively.
+            fn case_insensitive(a: &Value, b: &Value) -> Ordering {
+                a.as_str()
+                    .map(str::to_lowercase)
+                    .as_deref()
+                    .map(split_specifiers)
+                    .cmp(
+                        &b.as_str()
+                            .map(str::to_lowercase)
+                            .as_deref()
+                            .map(split_specifiers),
+                    )
+            }
+
+            /// Compare two [`Value`] requirements case-sensitively.
+            fn case_sensitive(a: &Value, b: &Value) -> Ordering {
+                a.as_str()
+                    .map(split_specifiers)
+                    .cmp(&b.as_str().map(split_specifiers))
+            }
+
             // Determine if the dependency list is sorted prior to
             // adding the new dependency; the new dependency list
             // will be sorted only when the original list is sorted
@@ -940,18 +962,11 @@ pub fn add_dependency(
                 .all(Value::is_str)
                 .then(|| {
                     if deps.iter().tuple_windows().all(|(a, b)| {
-                        a.as_str()
-                            .map(str::to_lowercase)
-                            .as_deref()
-                            .map(split_specifiers)
-                            <= b.as_str()
-                                .map(str::to_lowercase)
-                                .as_deref()
-                                .map(split_specifiers)
+                        matches!(case_insensitive(a, b), Ordering::Less | Ordering::Equal)
                     }) {
                         Some(Sort::CaseInsensitive)
                     } else if deps.iter().tuple_windows().all(|(a, b)| {
-                        a.as_str().map(split_specifiers) <= b.as_str().map(split_specifiers)
+                        matches!(case_sensitive(a, b), Ordering::Less | Ordering::Equal)
                     }) {
                         Some(Sort::CaseSensitive)
                     } else {
@@ -963,11 +978,11 @@ pub fn add_dependency(
 
             let req_string = req.to_string();
             let index = match sort {
-                Sort::CaseSensitive => deps
-                    .iter()
-                    .position(|d| d.as_str() > Some(req_string.as_str())),
                 Sort::CaseInsensitive => deps.iter().position(|d| {
-                    d.as_str().map(str::to_lowercase) > Some(req_string.as_str().to_lowercase())
+                    case_insensitive(d, &Value::from(req_string.as_str())) == Ordering::Greater
+                }),
+                Sort::CaseSensitive => deps.iter().position(|d| {
+                    case_sensitive(d, &Value::from(req_string.as_str())) == Ordering::Greater
                 }),
                 Sort::Unsorted => None,
             };
diff --git a/crates/uv/tests/it/edit.rs b/crates/uv/tests/it/edit.rs
index d0747e01c..5b7f90bb6 100644
--- a/crates/uv/tests/it/edit.rs
+++ b/crates/uv/tests/it/edit.rs
@@ -5853,29 +5853,30 @@ fn sorted_dependencies_name_specifiers() -> Result<()> {
 
     let pyproject_toml = context.temp_dir.child("pyproject.toml");
     pyproject_toml.write_str(indoc! {r#"
-    [project]
-    name = "project"
-    version = "0.1.0"
-    requires-python = ">=3.12"
-    dependencies = [
-        "typing>=3",
-        "typing-extensions>=4",
-    ]
+        [project]
+        name = "project"
+        version = "0.1.0"
+        requires-python = ">=3.12.0"
+        dependencies = [
+            "pytest>=8",
+            "typing-extensions>=4.10.0",
+        ]
     "#})?;
 
-    uv_snapshot!(context.filters(), context.add().args(["anyio"]), @r###"
+    uv_snapshot!(context.filters(), universal_windows_filters=true, context.add().args(["pytest-mock"]), @r###"
     success: true
     exit_code: 0
     ----- stdout -----
 
     ----- stderr -----
-    Resolved 6 packages in [TIME]
-    Prepared 5 packages in [TIME]
-    Installed 5 packages in [TIME]
-     + anyio==4.3.0
-     + idna==3.6
-     + sniffio==1.3.1
-     + typing==3.10.0.0
+    Resolved 8 packages in [TIME]
+    Prepared 6 packages in [TIME]
+    Installed 6 packages in [TIME]
+     + iniconfig==2.0.0
+     + packaging==24.0
+     + pluggy==1.4.0
+     + pytest==8.1.1
+     + pytest-mock==3.14.0
      + typing-extensions==4.10.0
     "###);
 
@@ -5889,15 +5890,49 @@ fn sorted_dependencies_name_specifiers() -> Result<()> {
         [project]
         name = "project"
         version = "0.1.0"
-        requires-python = ">=3.12"
+        requires-python = ">=3.12.[X]"
         dependencies = [
-            "anyio>=4.3.0",
-            "typing>=3",
-            "typing-extensions>=4",
+            "pytest>=8",
+            "pytest-mock>=3.14.0",
+            "typing-extensions>=4.10.0",
         ]
         "###
         );
     });
+
+    uv_snapshot!(context.filters(), universal_windows_filters=true, context.add().args(["pytest-randomly"]), @r###"
+    success: true
+    exit_code: 0
+    ----- stdout -----
+
+    ----- stderr -----
+    Resolved 9 packages in [TIME]
+    Prepared 1 package in [TIME]
+    Installed 1 package in [TIME]
+     + pytest-randomly==3.15.0
+    "###);
+
+    let pyproject_toml = context.read("pyproject.toml");
+
+    insta::with_settings!({
+        filters => context.filters(),
+    }, {
+        assert_snapshot!(
+            pyproject_toml, @r###"
+        [project]
+        name = "project"
+        version = "0.1.0"
+        requires-python = ">=3.12.[X]"
+        dependencies = [
+            "pytest>=8",
+            "pytest-mock>=3.14.0",
+            "pytest-randomly>=3.15.0",
+            "typing-extensions>=4.10.0",
+        ]
+        "###
+        );
+    });
+
     Ok(())
 }