diff --git a/crates/uv-workspace/src/pyproject_mut.rs b/crates/uv-workspace/src/pyproject_mut.rs
index dbfecf140b57d..3a76620d47f37 100644
--- a/crates/uv-workspace/src/pyproject_mut.rs
+++ b/crates/uv-workspace/src/pyproject_mut.rs
@@ -1009,8 +1009,12 @@ pub fn add_dependency(
             enum Sort {
                 /// The list is sorted in a case-insensitive manner.
                 CaseInsensitive,
+                /// The list is sorted naively in a case-insensitive manner.
+                CaseInsensitiveNaive,
                 /// The list is sorted in a case-sensitive manner.
                 CaseSensitive,
+                /// The list is sorted naively in a case-sensitive manner.
+                CaseSensitiveNaive,
                 /// The list is unsorted.
                 Unsorted,
             }
@@ -1029,6 +1033,13 @@ pub fn add_dependency(
                     )
             }
 
+            /// Naively compare two [`Value`] requirements case-insensitively.
+            fn case_insensitive_naive(a: &Value, b: &Value) -> Ordering {
+                a.as_str()
+                    .map(str::to_lowercase)
+                    .cmp(&b.as_str().map(str::to_lowercase))
+            }
+
             /// Compare two [`Value`] requirements case-sensitively.
             fn case_sensitive(a: &Value, b: &Value) -> Ordering {
                 a.as_str()
@@ -1036,6 +1047,11 @@ pub fn add_dependency(
                     .cmp(&b.as_str().map(split_specifiers))
             }
 
+            /// Naively compare two [`Value`] requirements case-sensitively.
+            fn case_sensitive_naive(a: &Value, b: &Value) -> Ordering {
+                a.as_str().cmp(&b.as_str())
+            }
+
             // 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
@@ -1057,6 +1073,17 @@ pub fn add_dependency(
                         matches!(case_sensitive(a, b), Ordering::Less | Ordering::Equal)
                     }) {
                         Some(Sort::CaseSensitive)
+                    } else if deps.iter().tuple_windows().all(|(a, b)| {
+                        matches!(
+                            case_insensitive_naive(a, b),
+                            Ordering::Less | Ordering::Equal
+                        )
+                    }) {
+                        Some(Sort::CaseInsensitiveNaive)
+                    } else if deps.iter().tuple_windows().all(|(a, b)| {
+                        matches!(case_sensitive_naive(a, b), Ordering::Less | Ordering::Equal)
+                    }) {
+                        Some(Sort::CaseSensitiveNaive)
                     } else {
                         None
                     }
@@ -1069,9 +1096,16 @@ pub fn add_dependency(
                 Sort::CaseInsensitive => deps.iter().position(|d| {
                     case_insensitive(d, &Value::from(req_string.as_str())) == Ordering::Greater
                 }),
+                Sort::CaseInsensitiveNaive => deps.iter().position(|d| {
+                    case_insensitive_naive(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::CaseSensitiveNaive => deps.iter().position(|d| {
+                    case_sensitive_naive(d, &Value::from(req_string.as_str())) == Ordering::Greater
+                }),
                 Sort::Unsorted => None,
             };
             let index = index.unwrap_or(deps.len());
diff --git a/crates/uv/tests/it/edit.rs b/crates/uv/tests/it/edit.rs
index d9b39a7e93ba5..160bbf4b79560 100644
--- a/crates/uv/tests/it/edit.rs
+++ b/crates/uv/tests/it/edit.rs
@@ -7240,6 +7240,63 @@ fn sorted_dependencies() -> Result<()> {
     Ok(())
 }
 
+/// Ensure that if the dependencies are sorted naively (i.e. by the whole
+/// requirement specifier), that added dependencies are sorted in the same way.
+#[test]
+fn naive_sorted_dependencies() -> Result<()> {
+    let context = TestContext::new("3.12").with_filtered_counts();
+
+    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 = [
+        "pytest-mock>=3.14",
+        "pytest>=8.1.1",
+    ]
+    "#})?;
+
+    uv_snapshot!(context.filters(), context.add().args(["pytest-randomly"]), @r"
+    success: true
+    exit_code: 0
+    ----- stdout -----
+
+    ----- stderr -----
+    Resolved [N] packages in [TIME]
+    Prepared [N] packages in [TIME]
+    Installed [N] packages in [TIME]
+     + iniconfig==2.0.0
+     + packaging==24.0
+     + pluggy==1.4.0
+     + pytest==8.1.1
+     + pytest-mock==3.14.0
+     + 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"
+        dependencies = [
+            "pytest-mock>=3.14",
+            "pytest-randomly>=3.15.0",
+            "pytest>=8.1.1",
+        ]
+        "###
+        );
+    });
+    Ok(())
+}
+
 /// Ensure that the added dependencies are case sensitive sorted if the dependency list was already
 /// case sensitive sorted prior to the operation.
 #[test]
@@ -7307,6 +7364,66 @@ fn case_sensitive_sorted_dependencies() -> Result<()> {
     Ok(())
 }
 
+/// Ensure that if the dependencies are sorted naively (i.e. by the whole
+/// requirement specifier), that added dependencies are sorted in the same way.
+#[test]
+fn case_sensitive_naive_sorted_dependencies() -> Result<()> {
+    let context = TestContext::new("3.12").with_filtered_counts();
+
+    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-extensions>=4.10.0",
+        "pytest-mock>=3.14",
+        "pytest>=8.1.1",
+    ]
+    "#})?;
+
+    uv_snapshot!(context.filters(), context.add().args(["pytest-randomly"]), @r"
+    success: true
+    exit_code: 0
+    ----- stdout -----
+
+    ----- stderr -----
+    Resolved [N] packages in [TIME]
+    Prepared [N] packages in [TIME]
+    Installed [N] packages in [TIME]
+     + iniconfig==2.0.0
+     + packaging==24.0
+     + pluggy==1.4.0
+     + pytest==8.1.1
+     + pytest-mock==3.14.0
+     + pytest-randomly==3.15.0
+     + typing-extensions==4.10.0
+    ");
+
+    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"
+        dependencies = [
+            "Typing-extensions>=4.10.0",
+            "pytest-mock>=3.14",
+            "pytest-randomly>=3.15.0",
+            "pytest>=8.1.1",
+        ]
+        "###
+        );
+    });
+    Ok(())
+}
+
 /// Ensure that sorting is based on the name, rather than the combined name-and-specifiers.
 #[test]
 fn sorted_dependencies_name_specifiers() -> Result<()> {