diff --git a/crates/ruff_formatter/src/builders.rs b/crates/ruff_formatter/src/builders.rs
index 3e34b4e25f..f5d81eb726 100644
--- a/crates/ruff_formatter/src/builders.rs
+++ b/crates/ruff_formatter/src/builders.rs
@@ -2155,15 +2155,18 @@ impl<Context> std::fmt::Debug for IndentIfGroupBreaks<'_, Context> {
     }
 }
 
-/// Changes the definition of *fits* for `content`. Instead of measuring it in *flat*, measure it with
-/// all line breaks expanded and test if no line exceeds the line width. The [`FitsExpanded`] acts
-/// as a expands boundary similar to best fitting, meaning that a [`hard_line_break`] will not cause the parent group to expand.
+/// Changes the definition of *fits* for `content`. It measures the width of all lines and allows
+/// the content inside of the [`fits_expanded`] to exceed the configured line width. The content
+/// coming before and after [`fits_expanded`] must fit into the configured line width.
+///
+/// The [`fits_expanded`] acts as a expands boundary similar to best fitting,
+/// meaning that a [`hard_line_break`] will not cause the parent group to expand.
 ///
 /// Useful in conjunction with a group with a condition.
 ///
 /// ## Examples
-/// The outer group with the binary expression remains *flat* regardless of the array expression
-/// that spans multiple lines.
+/// The outer group with the binary expression remains *flat* regardless of the array expression that
+/// spans multiple lines with items exceeding the configured line width.
 ///
 /// ```
 /// # use ruff_formatter::{format, format_args, LineWidth, SimpleFormatOptions, write};
@@ -2183,7 +2186,7 @@ impl<Context> std::fmt::Debug for IndentIfGroupBreaks<'_, Context> {
 ///                 token("["),
 ///                 soft_block_indent(&format_args![
 ///                     token("a,"), space(), token("# comment"), expand_parent(), soft_line_break_or_space(),
-///                     token("b")
+///                     token("'A very long string that exceeds the configured line width of 80 characters but the enclosing binary expression still fits.'")
 ///                 ]),
 ///                 token("]")
 ///             ]))
@@ -2194,7 +2197,7 @@ impl<Context> std::fmt::Debug for IndentIfGroupBreaks<'_, Context> {
 /// let formatted = format!(SimpleFormatContext::default(), [content])?;
 ///
 /// assert_eq!(
-///     "a + [\n\ta, # comment\n\tb\n]",
+///     "a + [\n\ta, # comment\n\t'A very long string that exceeds the configured line width of 80 characters but the enclosing binary expression still fits.'\n]",
 ///     formatted.print()?.as_code()
 /// );
 /// # Ok(())
diff --git a/crates/ruff_formatter/src/format_element/tag.rs b/crates/ruff_formatter/src/format_element/tag.rs
index 6e120a6381..e922425d20 100644
--- a/crates/ruff_formatter/src/format_element/tag.rs
+++ b/crates/ruff_formatter/src/format_element/tag.rs
@@ -84,11 +84,14 @@ pub enum Tag {
     StartFitsExpanded(FitsExpanded),
     EndFitsExpanded,
 
+    /// Marks the start and end of a best-fitting variant.
     StartBestFittingEntry,
     EndBestFittingEntry,
 
     /// Parenthesizes the content but only if adding the parentheses and indenting the content
     /// makes the content fit in the configured line width.
+    ///
+    /// See [`crate::builders::best_fit_parenthesize`] for an in-depth explanation.
     StartBestFitParenthesize {
         id: Option<GroupId>,
     },
diff --git a/crates/ruff_formatter/src/format_extensions.rs b/crates/ruff_formatter/src/format_extensions.rs
index da2d115001..e363757743 100644
--- a/crates/ruff_formatter/src/format_extensions.rs
+++ b/crates/ruff_formatter/src/format_extensions.rs
@@ -1,5 +1,3 @@
-#![allow(dead_code)]
-
 use crate::prelude::*;
 use std::cell::OnceCell;
 use std::marker::PhantomData;
diff --git a/crates/ruff_formatter/src/printer/mod.rs b/crates/ruff_formatter/src/printer/mod.rs
index 24f5f31c30..4535234fa3 100644
--- a/crates/ruff_formatter/src/printer/mod.rs
+++ b/crates/ruff_formatter/src/printer/mod.rs
@@ -1183,7 +1183,7 @@ impl<'a, 'print> FitsMeasurer<'a, 'print> {
                                 // line break should be printed as regular line break
                                 return Ok(Fits::Yes);
                             }
-                            MeasureMode::AllLines => {
+                            MeasureMode::AllLines | MeasureMode::AllLinesAllowTextOverflow => {
                                 // Continue measuring on the next line
                                 self.state.line_width = 0;
                                 self.state.pending_indent = args.indention();
@@ -1354,9 +1354,11 @@ impl<'a, 'print> FitsMeasurer<'a, 'print> {
             }
 
             FormatElement::Tag(StartLineSuffix { reserved_width }) => {
-                self.state.line_width += reserved_width;
-                if self.state.line_width > self.options().line_width.into() {
-                    return Ok(Fits::No);
+                if *reserved_width > 0 {
+                    self.state.line_width += reserved_width;
+                    if self.state.line_width > self.options().line_width.into() {
+                        return Ok(Fits::No);
+                    }
                 }
                 self.queue.skip_content(TagKind::LineSuffix);
                 self.state.has_line_suffix = true;
@@ -1370,32 +1372,42 @@ impl<'a, 'print> FitsMeasurer<'a, 'print> {
                 condition,
                 propagate_expand,
             })) => {
-                let condition_met = match condition {
-                    Some(condition) => {
-                        let group_mode = match condition.group_id {
-                            Some(group_id) => self.group_modes().get_print_mode(group_id)?,
-                            None => args.mode(),
+                match args.mode() {
+                    PrintMode::Expanded => {
+                        // As usual, nothing to measure
+                        self.stack.push(TagKind::FitsExpanded, args);
+                    }
+                    PrintMode::Flat => {
+                        let condition_met = match condition {
+                            Some(condition) => {
+                                let group_mode = match condition.group_id {
+                                    Some(group_id) => {
+                                        self.group_modes().get_print_mode(group_id)?
+                                    }
+                                    None => args.mode(),
+                                };
+
+                                condition.mode == group_mode
+                            }
+                            None => true,
                         };
 
-                        condition.mode == group_mode
-                    }
-                    None => true,
-                };
+                        if condition_met {
+                            // Measure in fully expanded mode and allow overflows
+                            self.stack.push(
+                                TagKind::FitsExpanded,
+                                args.with_measure_mode(MeasureMode::AllLinesAllowTextOverflow)
+                                    .with_print_mode(PrintMode::Expanded),
+                            );
+                        } else {
+                            if propagate_expand.get() {
+                                return Ok(Fits::No);
+                            }
 
-                if condition_met {
-                    // Measure in fully expanded mode.
-                    self.stack.push(
-                        TagKind::FitsExpanded,
-                        args.with_print_mode(PrintMode::Expanded)
-                            .with_measure_mode(MeasureMode::AllLines),
-                    );
-                } else {
-                    if propagate_expand.get() && args.mode().is_flat() {
-                        return Ok(Fits::No);
+                            // As usual
+                            self.stack.push(TagKind::FitsExpanded, args);
+                        }
                     }
-
-                    // As usual
-                    self.stack.push(TagKind::FitsExpanded, args);
                 }
             }
 
@@ -1482,7 +1494,8 @@ impl<'a, 'print> FitsMeasurer<'a, 'print> {
                                 }
                                 match args.measure_mode() {
                                     MeasureMode::FirstLine => return Fits::Yes,
-                                    MeasureMode::AllLines => {
+                                    MeasureMode::AllLines
+                                    | MeasureMode::AllLinesAllowTextOverflow => {
                                         self.state.line_width = 0;
                                         continue;
                                     }
@@ -1498,7 +1511,9 @@ impl<'a, 'print> FitsMeasurer<'a, 'print> {
             }
         }
 
-        if self.state.line_width > self.options().line_width.into() {
+        if self.state.line_width > self.options().line_width.into()
+            && !args.measure_mode().allows_text_overflow()
+        {
             return Fits::No;
         }
 
@@ -1601,6 +1616,17 @@ enum MeasureMode {
     /// The content only fits if none of the lines exceed the print width. Lines are terminated by either
     /// a hard line break or a soft line break in [`PrintMode::Expanded`].
     AllLines,
+
+    /// Measures all lines and allows lines to exceed the configured line width. Useful when it only matters
+    /// whether the content *before* and *after* fits.
+    AllLinesAllowTextOverflow,
+}
+
+impl MeasureMode {
+    /// Returns `true` if this mode allows text exceeding the configured line width.
+    const fn allows_text_overflow(self) -> bool {
+        matches!(self, MeasureMode::AllLinesAllowTextOverflow)
+    }
 }
 
 impl From<BestFittingMode> for MeasureMode {
diff --git a/crates/ruff_formatter/src/printer/printer_options/mod.rs b/crates/ruff_formatter/src/printer/printer_options/mod.rs
index c73ca1c62d..efbe850cbf 100644
--- a/crates/ruff_formatter/src/printer/printer_options/mod.rs
+++ b/crates/ruff_formatter/src/printer/printer_options/mod.rs
@@ -120,7 +120,6 @@ impl SourceMapGeneration {
     }
 }
 
-#[allow(dead_code)]
 #[derive(Copy, Clone, Debug, Eq, PartialEq, Default)]
 #[cfg_attr(feature = "serde", derive(serde::Serialize, serde::Deserialize))]
 pub enum LineEnding {
diff --git a/crates/ruff_python_formatter/resources/test/fixtures/ruff/expression/binary.py b/crates/ruff_python_formatter/resources/test/fixtures/ruff/expression/binary.py
index b77a52689d..3d08feaaf7 100644
--- a/crates/ruff_python_formatter/resources/test/fixtures/ruff/expression/binary.py
+++ b/crates/ruff_python_formatter/resources/test/fixtures/ruff/expression/binary.py
@@ -394,3 +394,15 @@ z = (
     # c: and this comment
     + a
 )
+
+# Test for https://github.com/astral-sh/ruff/issues/7431
+if True:
+    if True:
+        if True:
+            if True:
+                msg += " " + _(
+                    "Since the role is not mentionable, it will be momentarily made mentionable "
+                    "when announcing a streamalert. Please make sure I have the correct "
+                    "permissions to manage this role, or else members of this role won't receive "
+                    "a notification."
+                )
diff --git a/crates/ruff_python_formatter/resources/test/fixtures/ruff/expression/unsplittable.py b/crates/ruff_python_formatter/resources/test/fixtures/ruff/expression/unsplittable.py
index 4d46684bf5..b5f2c161c8 100644
--- a/crates/ruff_python_formatter/resources/test/fixtures/ruff/expression/unsplittable.py
+++ b/crates/ruff_python_formatter/resources/test/fixtures/ruff/expression/unsplittable.py
@@ -94,8 +94,3 @@ def f():
     aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa = (
         True
     )
-
-# Regression test for https://github.com/astral-sh/ruff/issues/7462
-if grid is not None:
-    rgrid = (rgrid.rio.reproject_match(grid, nodata=fillvalue) # rio.reproject nodata is use to initlialize the destination array
-             .where(~grid.isnull()))
diff --git a/crates/ruff_python_formatter/resources/test/fixtures/ruff/statement/assert.py b/crates/ruff_python_formatter/resources/test/fixtures/ruff/statement/assert.py
index b5ef028af1..ac127dd44a 100644
--- a/crates/ruff_python_formatter/resources/test/fixtures/ruff/statement/assert.py
+++ b/crates/ruff_python_formatter/resources/test/fixtures/ruff/statement/assert.py
@@ -153,3 +153,19 @@ def test():
             key9: value9,
         }
     ), "Not what we expected and the message is too long to fit in one lineeeeeeeeeeeeeee"
+
+# Test for https://github.com/astral-sh/ruff/issues/7246
+assert items == [
+    "a very very very very very very very very very very very very very very very long string",
+]
+
+assert package.files == [
+    {
+        "file": "pytest-3.5.0-py2.py3-none-any.whl",
+        "hash": "sha256:6266f87ab64692112e5477eba395cfedda53b1933ccd29478e671e73b420c19c",  # noqa: E501
+    },
+    {
+        "file": "pytest-3.5.0.tar.gz",
+        "hash": "sha256:fae491d1874f199537fd5872b5e1f0e74a009b979df9d53d1553fd03da1703e1",  # noqa: E501
+    },
+]
diff --git a/crates/ruff_python_formatter/src/expression/parentheses.rs b/crates/ruff_python_formatter/src/expression/parentheses.rs
index 134d4dcbb5..005b3efa05 100644
--- a/crates/ruff_python_formatter/src/expression/parentheses.rs
+++ b/crates/ruff_python_formatter/src/expression/parentheses.rs
@@ -155,32 +155,34 @@ impl<'content, 'ast> FormatParenthesized<'content, 'ast> {
 
 impl<'ast> Format<PyFormatContext<'ast>> for FormatParenthesized<'_, 'ast> {
     fn fmt(&self, f: &mut Formatter<PyFormatContext<'ast>>) -> FormatResult<()> {
-        let inner = format_with(|f| {
+        let current_level = f.context().node_level();
+
+        let content = format_with(|f| {
             group(&format_args![
-                token(self.left),
                 dangling_open_parenthesis_comments(self.comments),
-                soft_block_indent(&Arguments::from(&self.content)),
-                token(self.right)
+                soft_block_indent(&Arguments::from(&self.content))
             ])
             .fmt(f)
         });
 
-        let current_level = f.context().node_level();
+        let inner = format_with(|f| {
+            if let NodeLevel::Expression(Some(group_id)) = current_level {
+                // Use fits expanded if there's an enclosing group that adds the optional parentheses.
+                // This ensures that expanding this parenthesized expression does not expand the optional parentheses group.
+                write!(
+                    f,
+                    [fits_expanded(&content)
+                        .with_condition(Some(Condition::if_group_fits_on_line(group_id)))]
+                )
+            } else {
+                // It's not necessary to wrap the content if it is not inside of an optional_parentheses group.
+                content.fmt(f)
+            }
+        });
 
         let mut f = WithNodeLevel::new(NodeLevel::ParenthesizedExpression, f);
 
-        if let NodeLevel::Expression(Some(group_id)) = current_level {
-            // Use fits expanded if there's an enclosing group that adds the optional parentheses.
-            // This ensures that expanding this parenthesized expression does not expand the optional parentheses group.
-            write!(
-                f,
-                [fits_expanded(&inner)
-                    .with_condition(Some(Condition::if_group_fits_on_line(group_id)))]
-            )
-        } else {
-            // It's not necessary to wrap the content if it is not inside of an optional_parentheses group.
-            write!(f, [inner])
-        }
+        write!(f, [token(self.left), inner, token(self.right)])
     }
 }
 
diff --git a/crates/ruff_python_formatter/tests/snapshots/black_compatibility@simple_cases__trailing_comma_optional_parens3.py.snap b/crates/ruff_python_formatter/tests/snapshots/black_compatibility@simple_cases__trailing_comma_optional_parens3.py.snap
deleted file mode 100644
index d13dff5ee4..0000000000
--- a/crates/ruff_python_formatter/tests/snapshots/black_compatibility@simple_cases__trailing_comma_optional_parens3.py.snap
+++ /dev/null
@@ -1,77 +0,0 @@
----
-source: crates/ruff_python_formatter/tests/fixtures.rs
-input_file: crates/ruff_python_formatter/resources/test/fixtures/black/simple_cases/trailing_comma_optional_parens3.py
----
-## Input
-
-```py
-if True:
-    if True:
-        if True:
-            return _(
-                "qweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweas "
-                + "qweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqwegqweasdzxcqweasdzxc.",
-                "qweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqwe",
-            ) % {"reported_username": reported_username, "report_reason": report_reason}
-```
-
-## Black Differences
-
-```diff
---- Black
-+++ Ruff
-@@ -1,8 +1,14 @@
- if True:
-     if True:
-         if True:
--            return _(
--                "qweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweas "
--                + "qweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqwegqweasdzxcqweasdzxc.",
--                "qweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqwe",
--            ) % {"reported_username": reported_username, "report_reason": report_reason}
-+            return (
-+                _(
-+                    "qweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweas "
-+                    + "qweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqwegqweasdzxcqweasdzxc.",
-+                    "qweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqwe",
-+                )
-+                % {
-+                    "reported_username": reported_username,
-+                    "report_reason": report_reason,
-+                }
-+            )
-```
-
-## Ruff Output
-
-```py
-if True:
-    if True:
-        if True:
-            return (
-                _(
-                    "qweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweas "
-                    + "qweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqwegqweasdzxcqweasdzxc.",
-                    "qweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqwe",
-                )
-                % {
-                    "reported_username": reported_username,
-                    "report_reason": report_reason,
-                }
-            )
-```
-
-## Black Output
-
-```py
-if True:
-    if True:
-        if True:
-            return _(
-                "qweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweas "
-                + "qweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqwegqweasdzxcqweasdzxc.",
-                "qweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqweasdzxcqwe",
-            ) % {"reported_username": reported_username, "report_reason": report_reason}
-```
-
-
diff --git a/crates/ruff_python_formatter/tests/snapshots/format@expression__binary.py.snap b/crates/ruff_python_formatter/tests/snapshots/format@expression__binary.py.snap
index 849e9974cb..2c2ccd9b09 100644
--- a/crates/ruff_python_formatter/tests/snapshots/format@expression__binary.py.snap
+++ b/crates/ruff_python_formatter/tests/snapshots/format@expression__binary.py.snap
@@ -400,6 +400,18 @@ z = (
     # c: and this comment
     + a
 )
+
+# Test for https://github.com/astral-sh/ruff/issues/7431
+if True:
+    if True:
+        if True:
+            if True:
+                msg += " " + _(
+                    "Since the role is not mentionable, it will be momentarily made mentionable "
+                    "when announcing a streamalert. Please make sure I have the correct "
+                    "permissions to manage this role, or else members of this role won't receive "
+                    "a notification."
+                )
 ```
 
 ## Output
@@ -849,6 +861,18 @@ z = (
     # c: and this comment
     + a
 )
+
+# Test for https://github.com/astral-sh/ruff/issues/7431
+if True:
+    if True:
+        if True:
+            if True:
+                msg += " " + _(
+                    "Since the role is not mentionable, it will be momentarily made mentionable "
+                    "when announcing a streamalert. Please make sure I have the correct "
+                    "permissions to manage this role, or else members of this role won't receive "
+                    "a notification."
+                )
 ```
 
 
diff --git a/crates/ruff_python_formatter/tests/snapshots/format@expression__unsplittable.py.snap b/crates/ruff_python_formatter/tests/snapshots/format@expression__unsplittable.py.snap
index cd42bf3a36..1189d13a37 100644
--- a/crates/ruff_python_formatter/tests/snapshots/format@expression__unsplittable.py.snap
+++ b/crates/ruff_python_formatter/tests/snapshots/format@expression__unsplittable.py.snap
@@ -100,11 +100,6 @@ def f():
     aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa = (
         True
     )
-
-# Regression test for https://github.com/astral-sh/ruff/issues/7462
-if grid is not None:
-    rgrid = (rgrid.rio.reproject_match(grid, nodata=fillvalue) # rio.reproject nodata is use to initlialize the destination array
-             .where(~grid.isnull()))
 ```
 
 ## Output
@@ -227,15 +222,6 @@ def f():
     aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa = (
         True
     )
-
-
-# Regression test for https://github.com/astral-sh/ruff/issues/7462
-if grid is not None:
-    rgrid = rgrid.rio.reproject_match(
-        grid, nodata=fillvalue
-    ).where(  # rio.reproject nodata is use to initlialize the destination array
-        ~grid.isnull()
-    )
 ```
 
 
diff --git a/crates/ruff_python_formatter/tests/snapshots/format@statement__assert.py.snap b/crates/ruff_python_formatter/tests/snapshots/format@statement__assert.py.snap
index 534b604e8a..8f502dfe0a 100644
--- a/crates/ruff_python_formatter/tests/snapshots/format@statement__assert.py.snap
+++ b/crates/ruff_python_formatter/tests/snapshots/format@statement__assert.py.snap
@@ -159,6 +159,22 @@ def test():
             key9: value9,
         }
     ), "Not what we expected and the message is too long to fit in one lineeeeeeeeeeeeeee"
+
+# Test for https://github.com/astral-sh/ruff/issues/7246
+assert items == [
+    "a very very very very very very very very very very very very very very very long string",
+]
+
+assert package.files == [
+    {
+        "file": "pytest-3.5.0-py2.py3-none-any.whl",
+        "hash": "sha256:6266f87ab64692112e5477eba395cfedda53b1933ccd29478e671e73b420c19c",  # noqa: E501
+    },
+    {
+        "file": "pytest-3.5.0.tar.gz",
+        "hash": "sha256:fae491d1874f199537fd5872b5e1f0e74a009b979df9d53d1553fd03da1703e1",  # noqa: E501
+    },
+]
 ```
 
 ## Output
@@ -326,6 +342,23 @@ def test():
             key9: value9,
         }
     ), "Not what we expected and the message is too long to fit in one lineeeeeeeeeeeeeee"
+
+
+# Test for https://github.com/astral-sh/ruff/issues/7246
+assert items == [
+    "a very very very very very very very very very very very very very very very long string",
+]
+
+assert package.files == [
+    {
+        "file": "pytest-3.5.0-py2.py3-none-any.whl",
+        "hash": "sha256:6266f87ab64692112e5477eba395cfedda53b1933ccd29478e671e73b420c19c",  # noqa: E501
+    },
+    {
+        "file": "pytest-3.5.0.tar.gz",
+        "hash": "sha256:fae491d1874f199537fd5872b5e1f0e74a009b979df9d53d1553fd03da1703e1",  # noqa: E501
+    },
+]
 ```