sort dependencies in pyproject.toml (#6388)

## Summary
resolves #6203

## Test Plan
added a test fixing the bug described in the issue.

---------

Co-authored-by: konstin <konstin@mailbox.org>

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"] }

crates/uv-workspace/src/pyproject_mut.rs

@@ -1,12 +1,11 @@
+use itertools::Itertools;
+use pep440_rs::{Version, VersionSpecifier, VersionSpecifiers};
+use pep508_rs::{ExtraName, MarkerTree, PackageName, Requirement, VersionOrUrl};
 use std::path::Path;
 use std::str::FromStr;
 use std::{fmt, mem};
-
 use thiserror::Error;
 use toml_edit::{Array, DocumentMut, Item, RawString, Table, TomlError, Value};
-
-use pep440_rs::{Version, VersionSpecifier, VersionSpecifiers};
-use pep508_rs::{ExtraName, MarkerTree, PackageName, Requirement, VersionOrUrl};
 use uv_fs::PortablePath;
 
 use crate::pyproject::{DependencyType, Source};
@@ -522,13 +521,53 @@ 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() {
         [] => {
-            deps.push(req.to_string());
+            // 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 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
+                    .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_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(deps.len() - 1))
+
+            Ok(ArrayEdit::Add(index))
         }
         [_] => {
             let (i, mut old_req) = to_replace.remove(0);

crates/uv/tests/edit.rs

@@ -2310,8 +2310,8 @@ 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'",
         ]
 
         [build-system]
@@ -2348,8 +2348,8 @@ 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'",
         ]
 
         [build-system]
@@ -2390,8 +2390,8 @@ 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'",
         ]
 
@@ -2430,10 +2430,10 @@ 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'",
         ]
 
         [build-system]
@@ -3848,8 +3848,8 @@ fn add_requirements_file() -> Result<()> {
         version = "0.1.0"
         requires-python = ">=3.12"
         dependencies = [
-            "flask==2.3.2",
             "anyio",
+            "flask==2.3.2",
         ]
 
         [build-system]
@@ -3932,9 +3932,9 @@ fn add_script() -> Result<()> {
         # /// script
         # requires-python = ">=3.11"
         # dependencies = [
+        #   "anyio",
         #   "requests<3",
         #   "rich",
-        #   "anyio",
         # ]
         # ///
 
@@ -3984,8 +3984,8 @@ fn add_script_without_metadata_table() -> Result<()> {
         # /// script
         # requires-python = ">=3.12"
         # dependencies = [
-        #     "rich",
         #     "requests<3",
+        #     "rich",
         # ]
         # ///
         import requests
@@ -4036,8 +4036,8 @@ fn add_script_without_metadata_table_with_shebang() -> Result<()> {
         # /// script
         # requires-python = ">=3.12"
         # dependencies = [
-        #     "rich",
         #     "requests<3",
+        #     "rich",
         # ]
         # ///
         import requests
@@ -4092,8 +4092,8 @@ fn add_script_with_metadata_table_and_shebang() -> Result<()> {
         # /// script
         # requires-python = ">=3.12"
         # dependencies = [
-        #     "rich",
         #     "requests<3",
+        #     "rich",
         # ]
         # ///
         import requests
@@ -4143,8 +4143,8 @@ fn add_script_without_metadata_table_with_docstring() -> Result<()> {
         # /// script
         # requires-python = ">=3.12"
         # dependencies = [
-        #     "rich",
         #     "requests<3",
+        #     "rich",
         # ]
         # ///
         """This is a script."""
@@ -4410,3 +4410,115 @@ 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"]).arg("--frozen"), @r###"
+    success: true
+    exit_code: 0
+    ----- stdout -----
+
+    ----- stderr -----
+    "###);
+
+    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",
+        ]
+        "###
+        );
+    });
+    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"]).arg("--frozen"), @r###"
+    success: true
+    exit_code: 0
+    ----- stdout -----
+
+    ----- stderr -----
+    "###);
+
+    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",
+        ]
+        "###
+        );
+    });
+    Ok(())
+}