From 10426e15fe3e5a0172a35358f83e0140657b499a Mon Sep 17 00:00:00 2001
From: Chan Kang <chankang17@gmail.com>
Date: Sun, 25 Aug 2024 18:42:26 -0400
Subject: [PATCH 01/18] fix tests

---
 crates/uv-workspace/src/pyproject_mut.rs |  30 +++-
 crates/uv/tests/edit.rs                  | 168 ++++++++++++++++++++++-
 2 files changed, 188 insertions(+), 10 deletions(-)

diff --git a/crates/uv-workspace/src/pyproject_mut.rs b/crates/uv-workspace/src/pyproject_mut.rs
index cfb084fea45f..b5c67eda076f 100644
--- a/crates/uv-workspace/src/pyproject_mut.rs
+++ b/crates/uv-workspace/src/pyproject_mut.rs
@@ -3,10 +3,10 @@ use std::str::FromStr;
 use std::{fmt, mem};
 
 use pep440_rs::{Version, VersionSpecifier, VersionSpecifiers};
-use pep508_rs::{ExtraName, MarkerTree, PackageName, Requirement, VersionOrUrl};
+use pep508_rs::{ExtraName, MarkerTree, PackageName, Requirement, VerbatimUrl, VersionOrUrl};
 use thiserror::Error;
 use toml_edit::{Array, DocumentMut, Item, RawString, Table, TomlError, Value};
-use uv_fs::PortablePath;
+use uv_fs::{PortablePath, CWD};
 
 use crate::pyproject::{DependencyType, Source};
 
@@ -503,9 +503,20 @@ pub fn add_dependency(
     deps: &mut Array,
     has_source: bool,
 ) -> Result<ArrayEdit, Error> {
-    // Find matching dependencies.
     let mut to_replace = find_dependencies(&req.name, Some(&req.marker), deps);
-    match to_replace.as_slice() {
+
+    // determine 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
+    // so that users' custom dependency ordering is preserved.
+    let sorted = deps
+        .clone()
+        .into_iter()
+        .collect::<Vec<_>>()
+        .windows(2)
+        .all(|w| w[0].to_string() <= w[1].to_string());
+
+    let edit = match to_replace.as_slice() {
         [] => {
             deps.push(req.to_string());
             reformat_array_multiline(deps);
@@ -520,7 +531,18 @@ pub fn add_dependency(
         }
         // Cannot perform ambiguous updates.
         _ => Err(Error::Ambiguous),
+    };
+
+    if sorted {
+        deps.sort_by_key(|d| {
+            pep508_rs::Requirement::<VerbatimUrl>::parse(d.clone().as_str().unwrap(), &*CWD)
+                .unwrap()
+                .name
+                .clone()
+        })
     }
+
+    edit
 }
 
 /// Update an existing requirement.
diff --git a/crates/uv/tests/edit.rs b/crates/uv/tests/edit.rs
index c8425aa140c2..558f420a0c4f 100644
--- a/crates/uv/tests/edit.rs
+++ b/crates/uv/tests/edit.rs
@@ -3484,8 +3484,8 @@ fn add_requirements_file() -> Result<()> {
         # ...
         requires-python = ">=3.12"
         dependencies = [
-            "flask==2.3.2",
             "anyio",
+            "flask==2.3.2",
         ]
 
         [tool.uv.sources]
@@ -3564,9 +3564,9 @@ fn add_script() -> Result<()> {
         # /// script
         # requires-python = ">=3.11"
         # dependencies = [
+        #   "anyio",
         #   "requests<3",
         #   "rich",
-        #   "anyio",
         # ]
         # ///
 
@@ -3616,8 +3616,8 @@ fn add_script_without_metadata_table() -> Result<()> {
         # /// script
         # requires-python = ">=3.12"
         # dependencies = [
-        #     "rich",
         #     "requests<3",
+        #     "rich",
         # ]
         # ///
         import requests
@@ -3668,8 +3668,8 @@ fn add_script_without_metadata_table_with_shebang() -> Result<()> {
         # /// script
         # requires-python = ">=3.12"
         # dependencies = [
-        #     "rich",
         #     "requests<3",
+        #     "rich",
         # ]
         # ///
         import requests
@@ -3724,8 +3724,8 @@ fn add_script_with_metadata_table_and_shebang() -> Result<()> {
         # /// script
         # requires-python = ">=3.12"
         # dependencies = [
-        #     "rich",
         #     "requests<3",
+        #     "rich",
         # ]
         # ///
         import requests
@@ -3775,8 +3775,8 @@ fn add_script_without_metadata_table_with_docstring() -> Result<()> {
         # /// script
         # requires-python = ">=3.12"
         # dependencies = [
-        #     "rich",
         #     "requests<3",
+        #     "rich",
         # ]
         # ///
         """This is a script."""
@@ -4038,3 +4038,159 @@ fn fail_to_add_revert_project() -> Result<()> {
 
     Ok(())
 }
+
+/// Ensure that the added dependencies are sorted
+/// if the dependency list was already sorted prior to adding the new one.
+#[test]
+fn sorted_dependencies() -> Result<()> {
+    let context = TestContext::new("3.12");
+
+    let pyproject_toml = context.temp_dir.child("pyproject.toml");
+    pyproject_toml.write_str(indoc! {r#"
+    [project]
+    name = "project"
+    version = "0.1.0"
+    description = "Add your description here"
+    requires-python = ">=3.12"
+    dependencies = [
+        "CacheControl[filecache]>=0.14,<0.15",
+        "mwparserfromhell",
+        "pywikibot",
+        "sentry-sdk",
+        "yarl",
+    ]
+    "#})?;
+
+    uv_snapshot!(context.filters(), context.add(&["pydantic"]), @r###"
+    success: true
+    exit_code: 0
+    ----- stdout -----
+
+    ----- stderr -----
+    Resolved 19 packages in [TIME]
+    Prepared 19 packages in [TIME]
+    Installed 19 packages in [TIME]
+     + annotated-types==0.6.0
+     + cachecontrol==0.14.0
+     + certifi==2024.2.2
+     + charset-normalizer==3.3.2
+     + filelock==3.13.1
+     + idna==3.6
+     + msgpack==1.0.8
+     + multidict==6.0.5
+     + mwparserfromhell==0.6.6
+     + packaging==24.0
+     + project==0.1.0 (from file://[TEMP_DIR]/)
+     + pydantic==2.6.4
+     + pydantic-core==2.16.3
+     + pywikibot==9.0.0
+     + requests==2.31.0
+     + sentry-sdk==1.43.0
+     + typing-extensions==4.10.0
+     + urllib3==2.2.1
+     + yarl==1.9.4
+    "###);
+
+    let pyproject_toml = fs_err::read_to_string(context.temp_dir.join("pyproject.toml"))?;
+
+    insta::with_settings!({
+        filters => context.filters(),
+    }, {
+        assert_snapshot!(
+            pyproject_toml, @r###"
+        [project]
+        name = "project"
+        version = "0.1.0"
+        description = "Add your description here"
+        requires-python = ">=3.12"
+        dependencies = [
+            "CacheControl[filecache]>=0.14,<0.15",
+            "mwparserfromhell",
+            "pydantic",
+            "pywikibot",
+            "sentry-sdk",
+            "yarl>=2.6.4",
+        ]
+        "###
+        );
+    });
+    Ok(())
+}
+
+/// Ensure that the custom ordering of the dependencies is preserved
+/// after adding a package.
+#[test]
+fn custom_dependencies() -> Result<()> {
+    let context = TestContext::new("3.12");
+
+    let pyproject_toml = context.temp_dir.child("pyproject.toml");
+    pyproject_toml.write_str(indoc! {r#"
+    [project]
+    name = "project"
+    version = "0.1.0"
+    description = "Add your description here"
+    requires-python = ">=3.12"
+    dependencies = [
+        "yarl",
+        "CacheControl[filecache]>=0.14,<0.15",
+        "mwparserfromhell",
+        "pywikibot",
+        "sentry-sdk",
+    ]
+    "#})?;
+
+    uv_snapshot!(context.filters(), context.add(&["pydantic"]), @r###"
+    success: true
+    exit_code: 0
+    ----- stdout -----
+
+    ----- stderr -----
+    Resolved 19 packages in [TIME]
+    Prepared 19 packages in [TIME]
+    Installed 19 packages in [TIME]
+     + annotated-types==0.6.0
+     + cachecontrol==0.14.0
+     + certifi==2024.2.2
+     + charset-normalizer==3.3.2
+     + filelock==3.13.1
+     + idna==3.6
+     + msgpack==1.0.8
+     + multidict==6.0.5
+     + mwparserfromhell==0.6.6
+     + packaging==24.0
+     + project==0.1.0 (from file://[TEMP_DIR]/)
+     + pydantic==2.6.4
+     + pydantic-core==2.16.3
+     + pywikibot==9.0.0
+     + requests==2.31.0
+     + sentry-sdk==1.43.0
+     + typing-extensions==4.10.0
+     + urllib3==2.2.1
+     + yarl==1.9.4
+    "###);
+
+    let pyproject_toml = fs_err::read_to_string(context.temp_dir.join("pyproject.toml"))?;
+
+    insta::with_settings!({
+        filters => context.filters(),
+    }, {
+        assert_snapshot!(
+            pyproject_toml, @r###"
+        [project]
+        name = "project"
+        version = "0.1.0"
+        description = "Add your description here"
+        requires-python = ">=3.12"
+        dependencies = [
+            "yarl",
+            "CacheControl[filecache]>=0.14,<0.15",
+            "mwparserfromhell",
+            "pywikibot",
+            "sentry-sdk",
+            "pydantic>=2.6.4",
+        ]
+        "###
+        );
+    });
+    Ok(())
+}

From 9c131a5c7583d4e4bef39e5eb68eb718fd2e3ea2 Mon Sep 17 00:00:00 2001
From: Chan Kang <chankang17@gmail.com>
Date: Sun, 25 Aug 2024 18:47:25 -0400
Subject: [PATCH 02/18] clippy

---
 crates/uv-workspace/src/pyproject_mut.rs | 2 +-
 1 file changed, 1 insertion(+), 1 deletion(-)

diff --git a/crates/uv-workspace/src/pyproject_mut.rs b/crates/uv-workspace/src/pyproject_mut.rs
index b5c67eda076f..1a535578227b 100644
--- a/crates/uv-workspace/src/pyproject_mut.rs
+++ b/crates/uv-workspace/src/pyproject_mut.rs
@@ -539,7 +539,7 @@ pub fn add_dependency(
                 .unwrap()
                 .name
                 .clone()
-        })
+        });
     }
 
     edit

From 279f653d1348b23fee5e5d1089f3f72657bb8cd6 Mon Sep 17 00:00:00 2001
From: Chan Kang <chankang17@gmail.com>
Date: Sun, 25 Aug 2024 19:57:43 -0400
Subject: [PATCH 03/18] place the version constraint on the correct index

---
 crates/uv-workspace/src/pyproject_mut.rs | 56 ++++++++++++++----------
 1 file changed, 34 insertions(+), 22 deletions(-)

diff --git a/crates/uv-workspace/src/pyproject_mut.rs b/crates/uv-workspace/src/pyproject_mut.rs
index 1a535578227b..87f713ae1c5e 100644
--- a/crates/uv-workspace/src/pyproject_mut.rs
+++ b/crates/uv-workspace/src/pyproject_mut.rs
@@ -504,23 +504,44 @@ pub fn add_dependency(
     has_source: bool,
 ) -> Result<ArrayEdit, Error> {
     let mut to_replace = find_dependencies(&req.name, Some(&req.marker), deps);
-
-    // determine 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
-    // so that users' custom dependency ordering is preserved.
-    let sorted = deps
-        .clone()
-        .into_iter()
-        .collect::<Vec<_>>()
-        .windows(2)
-        .all(|w| w[0].to_string() <= w[1].to_string());
-
     let edit = match to_replace.as_slice() {
         [] => {
+            // determine 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
+            // so that users' custom dependency ordering is preserved.
+            let sorted = deps
+                .clone()
+                .into_iter()
+                .collect::<Vec<_>>()
+                .windows(2)
+                .all(|w| w[0].to_string() <= w[1].to_string());
+
             deps.push(req.to_string());
+            let mut index = deps.len() - 1;
+            if sorted {
+                deps.sort_by_key(|d| {
+                    pep508_rs::Requirement::<VerbatimUrl>::parse(d.clone().as_str().unwrap(), &*CWD)
+                        .unwrap()
+                        .name
+                        .clone()
+                });
+                index = deps
+                    .iter()
+                    .position(|d| {
+                        pep508_rs::Requirement::<VerbatimUrl>::parse(
+                            d.clone().as_str().unwrap(),
+                            &*CWD,
+                        )
+                        .unwrap()
+                        .name
+                            == req.name
+                    })
+                    .unwrap();
+            }
+
             reformat_array_multiline(deps);
-            Ok(ArrayEdit::Add(deps.len() - 1))
+            Ok(ArrayEdit::Add(index))
         }
         [_] => {
             let (i, mut old_req) = to_replace.remove(0);
@@ -533,15 +554,6 @@ pub fn add_dependency(
         _ => Err(Error::Ambiguous),
     };
 
-    if sorted {
-        deps.sort_by_key(|d| {
-            pep508_rs::Requirement::<VerbatimUrl>::parse(d.clone().as_str().unwrap(), &*CWD)
-                .unwrap()
-                .name
-                .clone()
-        });
-    }
-
     edit
 }
 

From 01ecc17c8a8362d590b991c675df4ae5da66f268 Mon Sep 17 00:00:00 2001
From: Chan Kang <chankang17@gmail.com>
Date: Sun, 25 Aug 2024 20:17:00 -0400
Subject: [PATCH 04/18] fix the test (should be failing)

---
 crates/uv-workspace/src/pyproject_mut.rs | 19 ++++---------------
 crates/uv/tests/edit.rs                  |  4 ++--
 2 files changed, 6 insertions(+), 17 deletions(-)

diff --git a/crates/uv-workspace/src/pyproject_mut.rs b/crates/uv-workspace/src/pyproject_mut.rs
index 87f713ae1c5e..1b003c749dab 100644
--- a/crates/uv-workspace/src/pyproject_mut.rs
+++ b/crates/uv-workspace/src/pyproject_mut.rs
@@ -504,6 +504,7 @@ pub fn add_dependency(
     has_source: bool,
 ) -> Result<ArrayEdit, Error> {
     let mut to_replace = find_dependencies(&req.name, Some(&req.marker), deps);
+
     let edit = match to_replace.as_slice() {
         [] => {
             // determine the dependency list is sorted prior to
@@ -518,7 +519,8 @@ pub fn add_dependency(
                 .all(|w| w[0].to_string() <= w[1].to_string());
 
             deps.push(req.to_string());
-            let mut index = deps.len() - 1;
+            reformat_array_multiline(deps);
+
             if sorted {
                 deps.sort_by_key(|d| {
                     pep508_rs::Requirement::<VerbatimUrl>::parse(d.clone().as_str().unwrap(), &*CWD)
@@ -526,22 +528,9 @@ pub fn add_dependency(
                         .name
                         .clone()
                 });
-                index = deps
-                    .iter()
-                    .position(|d| {
-                        pep508_rs::Requirement::<VerbatimUrl>::parse(
-                            d.clone().as_str().unwrap(),
-                            &*CWD,
-                        )
-                        .unwrap()
-                        .name
-                            == req.name
-                    })
-                    .unwrap();
             }
 
-            reformat_array_multiline(deps);
-            Ok(ArrayEdit::Add(index))
+            Ok(ArrayEdit::Add(deps.len() - 1))
         }
         [_] => {
             let (i, mut old_req) = to_replace.remove(0);
diff --git a/crates/uv/tests/edit.rs b/crates/uv/tests/edit.rs
index 558f420a0c4f..bead26675dfa 100644
--- a/crates/uv/tests/edit.rs
+++ b/crates/uv/tests/edit.rs
@@ -4106,10 +4106,10 @@ fn sorted_dependencies() -> Result<()> {
         dependencies = [
             "CacheControl[filecache]>=0.14,<0.15",
             "mwparserfromhell",
-            "pydantic",
+            "pydantic>=2.6.4",
             "pywikibot",
             "sentry-sdk",
-            "yarl>=2.6.4",
+            "yarl",
         ]
         "###
         );

From 7e3291eea8548c03596468cddcf7bd906c82227d Mon Sep 17 00:00:00 2001
From: Chan Kang <chankang17@gmail.com>
Date: Sun, 25 Aug 2024 21:38:32 -0400
Subject: [PATCH 05/18] index fix + need to fix more tests

---
 crates/uv-workspace/src/pyproject_mut.rs | 38 +++++++++++++-----------
 crates/uv/tests/edit.rs                  |  2 +-
 2 files changed, 21 insertions(+), 19 deletions(-)

diff --git a/crates/uv-workspace/src/pyproject_mut.rs b/crates/uv-workspace/src/pyproject_mut.rs
index 1b003c749dab..fe257b30e3a7 100644
--- a/crates/uv-workspace/src/pyproject_mut.rs
+++ b/crates/uv-workspace/src/pyproject_mut.rs
@@ -3,10 +3,10 @@ use std::str::FromStr;
 use std::{fmt, mem};
 
 use pep440_rs::{Version, VersionSpecifier, VersionSpecifiers};
-use pep508_rs::{ExtraName, MarkerTree, PackageName, Requirement, VerbatimUrl, VersionOrUrl};
+use pep508_rs::{ExtraName, MarkerTree, PackageName, Requirement, VersionOrUrl};
 use thiserror::Error;
 use toml_edit::{Array, DocumentMut, Item, RawString, Table, TomlError, Value};
-use uv_fs::{PortablePath, CWD};
+use uv_fs::PortablePath;
 
 use crate::pyproject::{DependencyType, Source};
 
@@ -504,33 +504,35 @@ pub fn add_dependency(
     has_source: bool,
 ) -> Result<ArrayEdit, Error> {
     let mut to_replace = find_dependencies(&req.name, Some(&req.marker), deps);
+    // determine 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
+    // so that users' custom dependency ordering is preserved.
+    let sorted = deps
+        .clone()
+        .into_iter()
+        .collect::<Vec<_>>()
+        .windows(2)
+        .all(|w| w[0].to_string() <= w[1].to_string());
 
     let edit = match to_replace.as_slice() {
         [] => {
-            // determine 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
-            // so that users' custom dependency ordering is preserved.
-            let sorted = deps
-                .clone()
-                .into_iter()
-                .collect::<Vec<_>>()
-                .windows(2)
-                .all(|w| w[0].to_string() <= w[1].to_string());
-
             deps.push(req.to_string());
             reformat_array_multiline(deps);
 
             if sorted {
                 deps.sort_by_key(|d| {
-                    pep508_rs::Requirement::<VerbatimUrl>::parse(d.clone().as_str().unwrap(), &*CWD)
+                    d.as_str()
+                        .and_then(try_parse_requirement)
                         .unwrap()
-                        .name
-                        .clone()
+                        .to_string()
                 });
             }
-
-            Ok(ArrayEdit::Add(deps.len() - 1))
+            let index = deps
+                .iter()
+                .position(|d| d.as_str().and_then(try_parse_requirement).unwrap().name == req.name)
+                .unwrap();
+            Ok(ArrayEdit::Add(index))
         }
         [_] => {
             let (i, mut old_req) = to_replace.remove(0);
diff --git a/crates/uv/tests/edit.rs b/crates/uv/tests/edit.rs
index bead26675dfa..798928be6c64 100644
--- a/crates/uv/tests/edit.rs
+++ b/crates/uv/tests/edit.rs
@@ -2077,8 +2077,8 @@ fn add_update_marker() -> Result<()> {
         version = "0.1.0"
         requires-python = ">=3.8"
         dependencies = [
-            "requests>=2.30; python_version >= '3.11'",
             "requests>=2.0,<2.29 ; python_full_version < '3.11'",
+            "requests>=2.30; python_version >= '3.11'",
         ]
         "###
         );

From c80112aa1d862ac1efd3956b67d2f29a49f0e818 Mon Sep 17 00:00:00 2001
From: Chan Kang <chankang17@gmail.com>
Date: Sun, 25 Aug 2024 21:52:23 -0400
Subject: [PATCH 06/18] fix add_update_marker

---
 crates/uv/tests/edit.rs | 8 ++++----
 1 file changed, 4 insertions(+), 4 deletions(-)

diff --git a/crates/uv/tests/edit.rs b/crates/uv/tests/edit.rs
index 798928be6c64..9e25ba942c06 100644
--- a/crates/uv/tests/edit.rs
+++ b/crates/uv/tests/edit.rs
@@ -2111,8 +2111,8 @@ fn add_update_marker() -> Result<()> {
         version = "0.1.0"
         requires-python = ">=3.8"
         dependencies = [
-            "requests>=2.30; python_version >= '3.11'",
             "requests>=2.0,<2.20 ; python_full_version < '3.11'",
+            "requests>=2.30; python_version >= '3.11'",
         ]
         "###
         );
@@ -2149,8 +2149,8 @@ fn add_update_marker() -> Result<()> {
         version = "0.1.0"
         requires-python = ">=3.8"
         dependencies = [
-            "requests>=2.30; python_version >= '3.11'",
             "requests>=2.0,<2.20 ; python_full_version < '3.11'",
+            "requests>=2.30; python_version >= '3.11'",
             "requests>=2.31 ; python_full_version >= '3.12' and sys_platform == 'win32'",
         ]
         "###
@@ -2185,10 +2185,10 @@ fn add_update_marker() -> Result<()> {
         version = "0.1.0"
         requires-python = ">=3.8"
         dependencies = [
-            "requests>=2.30; python_version >= '3.11'",
             "requests>=2.0,<2.20 ; python_full_version < '3.11'",
-            "requests>=2.31 ; python_full_version >= '3.12' and sys_platform == 'win32'",
             "requests>=2.10 ; sys_platform == 'win32'",
+            "requests>=2.30; python_version >= '3.11'",
+            "requests>=2.31 ; python_full_version >= '3.12' and sys_platform == 'win32'",
         ]
         "###
         );

From b98054f41aab5a6a9051002dc751cda2ab43d39d Mon Sep 17 00:00:00 2001
From: Chan Kang <chankang17@gmail.com>
Date: Sun, 25 Aug 2024 23:14:11 -0400
Subject: [PATCH 07/18] compare both name and extras

---
 crates/uv-workspace/src/pyproject_mut.rs | 3 ++-
 1 file changed, 2 insertions(+), 1 deletion(-)

diff --git a/crates/uv-workspace/src/pyproject_mut.rs b/crates/uv-workspace/src/pyproject_mut.rs
index fe257b30e3a7..f5846e0000e2 100644
--- a/crates/uv-workspace/src/pyproject_mut.rs
+++ b/crates/uv-workspace/src/pyproject_mut.rs
@@ -530,7 +530,8 @@ pub fn add_dependency(
             }
             let index = deps
                 .iter()
-                .position(|d| d.as_str().and_then(try_parse_requirement).unwrap().name == req.name)
+                .map(|d| d.as_str().and_then(try_parse_requirement).unwrap())
+                .position(|r| r.name == req.name && r.extras == req.extras)
                 .unwrap();
             Ok(ArrayEdit::Add(index))
         }

From 1217cc65c29766d70d366a92fa2e2754f2cb29da Mon Sep 17 00:00:00 2001
From: Chan Kang <chankang17@gmail.com>
Date: Sun, 25 Aug 2024 23:16:41 -0400
Subject: [PATCH 08/18] move 'sorted' into the conditional since it's only used
 inside

---
 crates/uv-workspace/src/pyproject_mut.rs | 21 +++++++++++----------
 1 file changed, 11 insertions(+), 10 deletions(-)

diff --git a/crates/uv-workspace/src/pyproject_mut.rs b/crates/uv-workspace/src/pyproject_mut.rs
index f5846e0000e2..50cd12942e57 100644
--- a/crates/uv-workspace/src/pyproject_mut.rs
+++ b/crates/uv-workspace/src/pyproject_mut.rs
@@ -504,19 +504,20 @@ pub fn add_dependency(
     has_source: bool,
 ) -> Result<ArrayEdit, Error> {
     let mut to_replace = find_dependencies(&req.name, Some(&req.marker), deps);
-    // determine 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
-    // so that users' custom dependency ordering is preserved.
-    let sorted = deps
-        .clone()
-        .into_iter()
-        .collect::<Vec<_>>()
-        .windows(2)
-        .all(|w| w[0].to_string() <= w[1].to_string());
 
     let edit = match to_replace.as_slice() {
         [] => {
+            // determine 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
+            // so that users' custom dependency ordering is preserved.
+            let sorted = deps
+                .clone()
+                .into_iter()
+                .collect::<Vec<_>>()
+                .windows(2)
+                .all(|w| w[0].to_string() <= w[1].to_string());
+
             deps.push(req.to_string());
             reformat_array_multiline(deps);
 

From acaf70315a5b61bdeeeb5f9f5aa5105ed48d54da Mon Sep 17 00:00:00 2001
From: Chan Kang <chankang17@gmail.com>
Date: Mon, 26 Aug 2024 10:29:12 -0400
Subject: [PATCH 09/18] remove unnecessary assignment

---
 crates/uv-workspace/src/pyproject_mut.rs | 6 ++----
 1 file changed, 2 insertions(+), 4 deletions(-)

diff --git a/crates/uv-workspace/src/pyproject_mut.rs b/crates/uv-workspace/src/pyproject_mut.rs
index 50cd12942e57..0357eeeaf515 100644
--- a/crates/uv-workspace/src/pyproject_mut.rs
+++ b/crates/uv-workspace/src/pyproject_mut.rs
@@ -505,7 +505,7 @@ pub fn add_dependency(
 ) -> Result<ArrayEdit, Error> {
     let mut to_replace = find_dependencies(&req.name, Some(&req.marker), deps);
 
-    let edit = match to_replace.as_slice() {
+    match to_replace.as_slice() {
         [] => {
             // determine the dependency list is sorted prior to
             // adding the new dependency; the new dependency list
@@ -545,9 +545,7 @@ pub fn add_dependency(
         }
         // Cannot perform ambiguous updates.
         _ => Err(Error::Ambiguous),
-    };
-
-    edit
+    }
 }
 
 /// Update an existing requirement.

From f454d23b018d40c80927a88a9ce93ac4663b75ff Mon Sep 17 00:00:00 2001
From: Chan Kang <chankang17@gmail.com>
Date: Mon, 26 Aug 2024 10:33:29 -0400
Subject: [PATCH 10/18] omit syncing in the tests

---
 crates/uv/tests/edit.rs | 46 ++---------------------------------------
 1 file changed, 2 insertions(+), 44 deletions(-)

diff --git a/crates/uv/tests/edit.rs b/crates/uv/tests/edit.rs
index 9e25ba942c06..68b6c837116f 100644
--- a/crates/uv/tests/edit.rs
+++ b/crates/uv/tests/edit.rs
@@ -4061,34 +4061,13 @@ fn sorted_dependencies() -> Result<()> {
     ]
     "#})?;
 
-    uv_snapshot!(context.filters(), context.add(&["pydantic"]), @r###"
+    uv_snapshot!(context.filters(), context.add(&["pydantic"]).arg("--no-sync"), @r###"
     success: true
     exit_code: 0
     ----- stdout -----
 
     ----- stderr -----
     Resolved 19 packages in [TIME]
-    Prepared 19 packages in [TIME]
-    Installed 19 packages in [TIME]
-     + annotated-types==0.6.0
-     + cachecontrol==0.14.0
-     + certifi==2024.2.2
-     + charset-normalizer==3.3.2
-     + filelock==3.13.1
-     + idna==3.6
-     + msgpack==1.0.8
-     + multidict==6.0.5
-     + mwparserfromhell==0.6.6
-     + packaging==24.0
-     + project==0.1.0 (from file://[TEMP_DIR]/)
-     + pydantic==2.6.4
-     + pydantic-core==2.16.3
-     + pywikibot==9.0.0
-     + requests==2.31.0
-     + sentry-sdk==1.43.0
-     + typing-extensions==4.10.0
-     + urllib3==2.2.1
-     + yarl==1.9.4
     "###);
 
     let pyproject_toml = fs_err::read_to_string(context.temp_dir.join("pyproject.toml"))?;
@@ -4139,34 +4118,13 @@ fn custom_dependencies() -> Result<()> {
     ]
     "#})?;
 
-    uv_snapshot!(context.filters(), context.add(&["pydantic"]), @r###"
+    uv_snapshot!(context.filters(), context.add(&["pydantic"]).arg("--no-sync"), @r###"
     success: true
     exit_code: 0
     ----- stdout -----
 
     ----- stderr -----
     Resolved 19 packages in [TIME]
-    Prepared 19 packages in [TIME]
-    Installed 19 packages in [TIME]
-     + annotated-types==0.6.0
-     + cachecontrol==0.14.0
-     + certifi==2024.2.2
-     + charset-normalizer==3.3.2
-     + filelock==3.13.1
-     + idna==3.6
-     + msgpack==1.0.8
-     + multidict==6.0.5
-     + mwparserfromhell==0.6.6
-     + packaging==24.0
-     + project==0.1.0 (from file://[TEMP_DIR]/)
-     + pydantic==2.6.4
-     + pydantic-core==2.16.3
-     + pywikibot==9.0.0
-     + requests==2.31.0
-     + sentry-sdk==1.43.0
-     + typing-extensions==4.10.0
-     + urllib3==2.2.1
-     + yarl==1.9.4
     "###);
 
     let pyproject_toml = fs_err::read_to_string(context.temp_dir.join("pyproject.toml"))?;

From 2659dc72489f3b8401d8e198a5bacb311f2e3926 Mon Sep 17 00:00:00 2001
From: Chan Kang <chankang17@gmail.com>
Date: Mon, 26 Aug 2024 13:10:16 -0400
Subject: [PATCH 11/18] add itertools to uv-workspace

---
 Cargo.lock                     | 1 +
 crates/uv-workspace/Cargo.toml | 1 +
 2 files changed, 2 insertions(+)

diff --git a/Cargo.lock b/Cargo.lock
index 31bd8ab4ea42..7d23463a69e7 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -5319,6 +5319,7 @@ dependencies = [
  "fs-err",
  "glob",
  "insta",
+ "itertools 0.13.0",
  "pep440_rs",
  "pep508_rs",
  "pypi-types",
diff --git a/crates/uv-workspace/Cargo.toml b/crates/uv-workspace/Cargo.toml
index 7b5a40473cfa..909e682b3712 100644
--- a/crates/uv-workspace/Cargo.toml
+++ b/crates/uv-workspace/Cargo.toml
@@ -35,6 +35,7 @@ toml =  { workspace = true }
 toml_edit =  { workspace = true }
 tracing = { workspace = true }
 url = { workspace = true }
+itertools = { workspace = true }
 
 [dev-dependencies]
 insta = { version = "1.39.0", features = ["filters", "json", "redactions"] }

From 99345448808f967b2b171fa6aafb12bb169e2bec Mon Sep 17 00:00:00 2001
From: Chan Kang <chankang17@gmail.com>
Date: Tue, 27 Aug 2024 12:24:46 -0400
Subject: [PATCH 12/18] need to fix reformatting

---
 crates/uv-workspace/src/pyproject_mut.rs | 27 ++++++++++++------------
 1 file changed, 13 insertions(+), 14 deletions(-)

diff --git a/crates/uv-workspace/src/pyproject_mut.rs b/crates/uv-workspace/src/pyproject_mut.rs
index 0357eeeaf515..9df02ab10cee 100644
--- a/crates/uv-workspace/src/pyproject_mut.rs
+++ b/crates/uv-workspace/src/pyproject_mut.rs
@@ -2,6 +2,7 @@ use std::path::Path;
 use std::str::FromStr;
 use std::{fmt, mem};
 
+use itertools::partition;
 use pep440_rs::{Version, VersionSpecifier, VersionSpecifiers};
 use pep508_rs::{ExtraName, MarkerTree, PackageName, Requirement, VersionOrUrl};
 use thiserror::Error;
@@ -518,22 +519,20 @@ pub fn add_dependency(
                 .windows(2)
                 .all(|w| w[0].to_string() <= w[1].to_string());
 
-            deps.push(req.to_string());
+            let mut index = deps.len();
+            if sorted {
+                index = partition(
+                    &mut deps.clone().into_iter().collect::<Vec<_>>(),
+                    |d: &Value| {
+                        *d.to_string()
+                            .trim_matches(|c| c == '\"' || c == ' ' || c == '\n')
+                            < *req.to_string()
+                    },
+                );
+            };
+            deps.insert(index, req.to_string());
             reformat_array_multiline(deps);
 
-            if sorted {
-                deps.sort_by_key(|d| {
-                    d.as_str()
-                        .and_then(try_parse_requirement)
-                        .unwrap()
-                        .to_string()
-                });
-            }
-            let index = deps
-                .iter()
-                .map(|d| d.as_str().and_then(try_parse_requirement).unwrap())
-                .position(|r| r.name == req.name && r.extras == req.extras)
-                .unwrap();
             Ok(ArrayEdit::Add(index))
         }
         [_] => {

From fe7fbfe08c74e4f76cc26a795d04416369f4502f Mon Sep 17 00:00:00 2001
From: Chan Kang <chankang17@gmail.com>
Date: Tue, 27 Aug 2024 16:15:58 -0400
Subject: [PATCH 13/18] handle the indentation edge case

---
 crates/uv-workspace/src/pyproject_mut.rs | 18 ++++++++++++++++++
 1 file changed, 18 insertions(+)

diff --git a/crates/uv-workspace/src/pyproject_mut.rs b/crates/uv-workspace/src/pyproject_mut.rs
index 9df02ab10cee..2b5a0a570c0d 100644
--- a/crates/uv-workspace/src/pyproject_mut.rs
+++ b/crates/uv-workspace/src/pyproject_mut.rs
@@ -530,7 +530,25 @@ pub fn add_dependency(
                     },
                 );
             };
+
             deps.insert(index, req.to_string());
+            // `reformat_array_multiline` uses the indentation of the first dependency entry.
+            // Therefore, we retrieve the indentation of the first dependency entry and apply it to the new entry.
+            // Note that it is only necessary if the newly added dependency is going to be the first in the list
+            // _and_ the dependency list was not empty prior to adding the new dependency.
+            if deps.len() > 1 && index == 0 {
+                let prefix = deps
+                    .clone()
+                    .get(index + 1)
+                    .unwrap()
+                    .decor()
+                    .prefix()
+                    .unwrap()
+                    .clone();
+
+                deps.get_mut(index).unwrap().decor_mut().set_prefix(prefix);
+            }
+
             reformat_array_multiline(deps);
 
             Ok(ArrayEdit::Add(index))

From e1e55f92bda9d501ef8b1e7b2dfc1ed48b15c442 Mon Sep 17 00:00:00 2001
From: Chan Kang <chankang17@gmail.com>
Date: Tue, 27 Aug 2024 16:36:39 -0400
Subject: [PATCH 14/18] add check for str

---
 crates/uv-workspace/src/pyproject_mut.rs | 18 ++++++++++--------
 1 file changed, 10 insertions(+), 8 deletions(-)

diff --git a/crates/uv-workspace/src/pyproject_mut.rs b/crates/uv-workspace/src/pyproject_mut.rs
index 2b5a0a570c0d..38fa492e72c6 100644
--- a/crates/uv-workspace/src/pyproject_mut.rs
+++ b/crates/uv-workspace/src/pyproject_mut.rs
@@ -508,17 +508,19 @@ pub fn add_dependency(
 
     match to_replace.as_slice() {
         [] => {
-            // determine the dependency list is sorted prior to
+            // Determine 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
             // so that users' custom dependency ordering is preserved.
-            let sorted = deps
-                .clone()
-                .into_iter()
-                .collect::<Vec<_>>()
-                .windows(2)
-                .all(|w| w[0].to_string() <= w[1].to_string());
-
+            // Additionallly, if the table is invalid (i.e. contains non-string values)
+            // we still treat it as unsorted for the sake of simplicity.
+            let sorted = deps.iter().all(|d| d.is_str())
+                && deps
+                    .clone()
+                    .into_iter()
+                    .collect::<Vec<_>>()
+                    .windows(2)
+                    .all(|w| w[0].to_string() <= w[1].to_string());
             let mut index = deps.len();
             if sorted {
                 index = partition(

From 7f33e71ea30ed839ff95e84b7ff4fe8b839124be Mon Sep 17 00:00:00 2001
From: Chan Kang <chankang17@gmail.com>
Date: Tue, 27 Aug 2024 18:06:30 -0400
Subject: [PATCH 15/18] clippy

---
 crates/uv-workspace/src/pyproject_mut.rs | 2 +-
 1 file changed, 1 insertion(+), 1 deletion(-)

diff --git a/crates/uv-workspace/src/pyproject_mut.rs b/crates/uv-workspace/src/pyproject_mut.rs
index 38fa492e72c6..6a933e26d466 100644
--- a/crates/uv-workspace/src/pyproject_mut.rs
+++ b/crates/uv-workspace/src/pyproject_mut.rs
@@ -514,7 +514,7 @@ pub fn add_dependency(
             // so that users' custom dependency ordering is preserved.
             // Additionallly, if the table is invalid (i.e. contains non-string values)
             // we still treat it as unsorted for the sake of simplicity.
-            let sorted = deps.iter().all(|d| d.is_str())
+            let sorted = deps.iter().all(toml_edit::Value::is_str)
                 && deps
                     .clone()
                     .into_iter()

From 4e3031dacca2d3474dabc344f8216a151f70492e Mon Sep 17 00:00:00 2001
From: Chan Kang <chankang17@gmail.com>
Date: Tue, 27 Aug 2024 18:10:05 -0400
Subject: [PATCH 16/18] fix typo

---
 crates/uv-workspace/src/pyproject_mut.rs | 2 +-
 1 file changed, 1 insertion(+), 1 deletion(-)

diff --git a/crates/uv-workspace/src/pyproject_mut.rs b/crates/uv-workspace/src/pyproject_mut.rs
index 6a933e26d466..e896c22e2295 100644
--- a/crates/uv-workspace/src/pyproject_mut.rs
+++ b/crates/uv-workspace/src/pyproject_mut.rs
@@ -512,7 +512,7 @@ pub fn add_dependency(
             // adding the new dependency; the new dependency list
             // will be sorted only when the original list is sorted
             // so that users' custom dependency ordering is preserved.
-            // Additionallly, if the table is invalid (i.e. contains non-string values)
+            // Additionally, if the table is invalid (i.e. contains non-string values)
             // we still treat it as unsorted for the sake of simplicity.
             let sorted = deps.iter().all(toml_edit::Value::is_str)
                 && deps

From db2af8537d1af8c3feb18d2653df83d35467f24c Mon Sep 17 00:00:00 2001
From: konstin <konstin@mailbox.org>
Date: Thu, 29 Aug 2024 16:03:40 +0200
Subject: [PATCH 17/18] Don't lock on sortedness tests

---
 crates/uv/tests/edit.rs | 10 ++++------
 1 file changed, 4 insertions(+), 6 deletions(-)

diff --git a/crates/uv/tests/edit.rs b/crates/uv/tests/edit.rs
index 68b6c837116f..75c3c67b3248 100644
--- a/crates/uv/tests/edit.rs
+++ b/crates/uv/tests/edit.rs
@@ -4061,13 +4061,12 @@ fn sorted_dependencies() -> Result<()> {
     ]
     "#})?;
 
-    uv_snapshot!(context.filters(), context.add(&["pydantic"]).arg("--no-sync"), @r###"
+    uv_snapshot!(context.filters(), context.add(&["pydantic"]).arg("--frozen"), @r###"
     success: true
     exit_code: 0
     ----- stdout -----
 
     ----- stderr -----
-    Resolved 19 packages in [TIME]
     "###);
 
     let pyproject_toml = fs_err::read_to_string(context.temp_dir.join("pyproject.toml"))?;
@@ -4085,7 +4084,7 @@ fn sorted_dependencies() -> Result<()> {
         dependencies = [
             "CacheControl[filecache]>=0.14,<0.15",
             "mwparserfromhell",
-            "pydantic>=2.6.4",
+            "pydantic",
             "pywikibot",
             "sentry-sdk",
             "yarl",
@@ -4118,13 +4117,12 @@ fn custom_dependencies() -> Result<()> {
     ]
     "#})?;
 
-    uv_snapshot!(context.filters(), context.add(&["pydantic"]).arg("--no-sync"), @r###"
+    uv_snapshot!(context.filters(), context.add(&["pydantic"]).arg("--frozen"), @r###"
     success: true
     exit_code: 0
     ----- stdout -----
 
     ----- stderr -----
-    Resolved 19 packages in [TIME]
     "###);
 
     let pyproject_toml = fs_err::read_to_string(context.temp_dir.join("pyproject.toml"))?;
@@ -4145,7 +4143,7 @@ fn custom_dependencies() -> Result<()> {
             "mwparserfromhell",
             "pywikibot",
             "sentry-sdk",
-            "pydantic>=2.6.4",
+            "pydantic",
         ]
         "###
         );

From c27bf33c1d212190e398b30342d191e7ea54fcde Mon Sep 17 00:00:00 2001
From: konstin <konstin@mailbox.org>
Date: Thu, 29 Aug 2024 16:19:21 +0200
Subject: [PATCH 18/18] Simplify sorting logic

---
 crates/uv-workspace/src/pyproject_mut.rs | 41 +++++++++++-------------
 1 file changed, 19 insertions(+), 22 deletions(-)

diff --git a/crates/uv-workspace/src/pyproject_mut.rs b/crates/uv-workspace/src/pyproject_mut.rs
index e896c22e2295..8eb2a6ef854c 100644
--- a/crates/uv-workspace/src/pyproject_mut.rs
+++ b/crates/uv-workspace/src/pyproject_mut.rs
@@ -2,7 +2,7 @@ use std::path::Path;
 use std::str::FromStr;
 use std::{fmt, mem};
 
-use itertools::partition;
+use itertools::Itertools;
 use pep440_rs::{Version, VersionSpecifier, VersionSpecifiers};
 use pep508_rs::{ExtraName, MarkerTree, PackageName, Requirement, VersionOrUrl};
 use thiserror::Error;
@@ -508,36 +508,33 @@ pub fn add_dependency(
 
     match to_replace.as_slice() {
         [] => {
-            // Determine the dependency list is sorted prior to
+            // 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
-            // so that users' custom dependency ordering is preserved.
+            // so that user's custom dependency ordering is preserved.
             // Additionally, if the table is invalid (i.e. contains non-string values)
             // we still treat it as unsorted for the sake of simplicity.
             let sorted = deps.iter().all(toml_edit::Value::is_str)
                 && deps
-                    .clone()
-                    .into_iter()
-                    .collect::<Vec<_>>()
-                    .windows(2)
-                    .all(|w| w[0].to_string() <= w[1].to_string());
-            let mut index = deps.len();
-            if sorted {
-                index = partition(
-                    &mut deps.clone().into_iter().collect::<Vec<_>>(),
-                    |d: &Value| {
-                        *d.to_string()
-                            .trim_matches(|c| c == '\"' || c == ' ' || c == '\n')
-                            < *req.to_string()
-                    },
-                );
+                    .iter()
+                    .tuple_windows()
+                    .all(|(a, b)| a.as_str() <= b.as_str());
+
+            let req_string = req.to_string();
+            let index = if sorted {
+                deps.iter()
+                    .position(|d: &Value| d.as_str() > Some(req_string.as_str()))
+                    .unwrap_or(deps.len())
+            } else {
+                deps.len()
             };
 
-            deps.insert(index, req.to_string());
+            deps.insert(index, req_string);
             // `reformat_array_multiline` uses the indentation of the first dependency entry.
-            // Therefore, we retrieve the indentation of the first dependency entry and apply it to the new entry.
-            // Note that it is only necessary if the newly added dependency is going to be the first in the list
-            // _and_ the dependency list was not empty prior to adding the new dependency.
+            // Therefore, we retrieve the indentation of the first dependency entry and apply it to
+            // the new entry. Note that it is only necessary if the newly added dependency is going
+            // to be the first in the list _and_ the dependency list was not empty prior to adding
+            // the new dependency.
             if deps.len() > 1 && index == 0 {
                 let prefix = deps
                     .clone()