From 2f88f849726d50de91efc48ac0148395b7231cd0 Mon Sep 17 00:00:00 2001
From: Micha Reiser <micha@reiser.io>
Date: Wed, 23 Oct 2024 07:57:53 +0200
Subject: [PATCH] Alternate quotes for strings inside f-strings in preview
 (#13860)

---
 crates/ruff_dev/src/format_dev.rs             |   5 +-
 crates/ruff_python_ast/src/expression.rs      |   4 +
 .../test/fixtures/ruff/expression/fstring.py  |  35 +-
 .../fixtures/ruff/expression/fstring_py312.py |  11 +
 .../src/other/f_string.rs                     |  37 +-
 .../src/other/f_string_element.rs             |  18 +-
 crates/ruff_python_formatter/src/preview.rs   |   2 +
 .../src/string/normalize.rs                   | 333 +++++++++++++++---
 ...bility@cases__preview_long_strings.py.snap |   8 +-
 ...__preview_long_strings__regression.py.snap |   8 +-
 .../format@expression__fstring.py.snap        | 170 +++++++--
 .../format@expression__fstring_py312.py.snap  |  43 ++-
 12 files changed, 556 insertions(+), 118 deletions(-)

diff --git a/crates/ruff_dev/src/format_dev.rs b/crates/ruff_dev/src/format_dev.rs
index 2ef361a46d69b..f9be6b0bf591a 100644
--- a/crates/ruff_dev/src/format_dev.rs
+++ b/crates/ruff_dev/src/format_dev.rs
@@ -251,8 +251,7 @@ pub(crate) fn main(args: &Args) -> anyhow::Result<ExitCode> {
         }
         info!(
             parent: None,
-            "Done: {} stability errors, {} files, similarity index {:.5}), files with differences: {} took {:.2}s, {} input files contained syntax errors ",
-            error_count,
+            "Done: {error_count} stability/syntax errors, {} files, similarity index {:.5}), files with differences: {} took {:.2}s, {} input files contained syntax errors ",
             result.file_count,
             result.statistics.similarity_index(),
             result.statistics.files_with_differences,
@@ -796,7 +795,7 @@ impl CheckFileError {
             | CheckFileError::PrintError(_)
             | CheckFileError::Panic { .. } => false,
             #[cfg(not(debug_assertions))]
-            CheckFileError::Slow(_) => false,
+            CheckFileError::Slow(_) => true,
         }
     }
 }
diff --git a/crates/ruff_python_ast/src/expression.rs b/crates/ruff_python_ast/src/expression.rs
index a4a9c044ba08c..6fb0ef9d29306 100644
--- a/crates/ruff_python_ast/src/expression.rs
+++ b/crates/ruff_python_ast/src/expression.rs
@@ -524,6 +524,10 @@ impl StringLikePart<'_> {
             self.end() - kind.closer_len(),
         )
     }
+
+    pub const fn is_fstring(self) -> bool {
+        matches!(self, Self::FString(_))
+    }
 }
 
 impl<'a> From<&'a ast::StringLiteral> for StringLikePart<'a> {
diff --git a/crates/ruff_python_formatter/resources/test/fixtures/ruff/expression/fstring.py b/crates/ruff_python_formatter/resources/test/fixtures/ruff/expression/fstring.py
index 69f65c20c573a..3c895ee85aeb4 100644
--- a/crates/ruff_python_formatter/resources/test/fixtures/ruff/expression/fstring.py
+++ b/crates/ruff_python_formatter/resources/test/fixtures/ruff/expression/fstring.py
@@ -94,6 +94,8 @@
                                              "bbbbbbbbbbbbbbbbbbbbbbbbbbbbb" } ccccccccccccccc"
 x = f"aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa { # comment 9
                                              "bbbbbbbbbbbbbbbbbbbbbbbbbbbbb" = } ccccccccccccccc"
+x = f"aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa { # comment 9
+                                             'bbbbbbbbbbbbbbbbbbbbbbbbbbbbb' = } ccccccccccccccc"
 
 # Multiple larger expressions which exceeds the line length limit. Here, we need to decide
 # whether to split at the first or second expression. This should work similarly to the
@@ -144,18 +146,37 @@
     {'aaaaaaaaaaaaaaaaaaaaaaaaa', 'bbbbbbbbbbbbbbbbbbbbbbbbbbb', 'cccccccccccccccccccccccccc'}
 }"
 
+#############################################################################################
 # Quotes
+#############################################################################################
 f"foo 'bar' {x}"
 f"foo \"bar\" {x}"
 f'foo "bar" {x}'
 f'foo \'bar\' {x}'
 f"foo {"bar"}"
-f"foo {'\'bar\''}"
+
+f"single quoted '{x}' double quoted \"{x}\"" # Same number of quotes => use preferred quote style
+f"single quote ' {x} double quoted \"{x}\""  # More double quotes => use single quotes
+f"single quoted '{x}' double quote \" {x}"  # More single quotes => use double quotes
+
+fr"single quotes ' {x}"  # Keep double because `'` can't be escaped
+fr'double quotes " {x}'  # Keep single because `"` can't be escaped
+fr'flip quotes {x}'  # Use preferred quotes, because raw string contains now quotes.
 
 # Here, the formatter will remove the escapes which is correct because they aren't allowed
 # pre 3.12. This means we can assume that the f-string is used in the context of 3.12.
+f"foo {'\'bar\''}"
 f"foo {'\"bar\"'}"
 
+# Quotes inside the expressions have no impact on the quote selection of the outer string.
+# Required so that the following two examples result in the same formatting.
+f'foo {10 + len("bar")}'
+f"foo {10 + len('bar')}"
+
+# Pre 312, preserve the outer quotes if the f-string contains quotes in the debug expression
+f'foo {10 + len("bar")=}'
+f'''foo {10 + len('''bar''')=}'''
+f'''foo {10 + len('bar')=}'''  # Fine to change the quotes because it uses triple quotes
 
 # Triple-quoted strings
 # It's ok to use the same quote char for the inner string if it's single-quoted.
@@ -164,6 +185,16 @@
 # But if the inner string is also triple-quoted then we should preserve the existing quotes.
 f"""test {'''inner'''}"""
 
+# It's not okay to change the quote style if the inner string is triple quoted and contains a quote.
+f'{"""other " """}'
+f'{"""other " """ + "more"}'
+f'{b"""other " """}'
+f'{f"""other " """}'
+
+# Not valid Pre 3.12
+f"""test {f'inner {'''inner inner'''}'}"""
+f"""test {f'''inner {"""inner inner"""}'''}"""
+
 # Magic trailing comma
 #
 # The expression formatting will result in breaking it across multiple lines with a
@@ -312,6 +343,6 @@
 # Implicit concatenated f-string containing quotes
 _ = (
     'This string should change its quotes to double quotes'
-    f'This string uses double quotes in an expression {"woah"}'
+    f'This string uses double quotes in an expression {"it's a quote"}'
     f'This f-string does not use any quotes.'
 )
diff --git a/crates/ruff_python_formatter/resources/test/fixtures/ruff/expression/fstring_py312.py b/crates/ruff_python_formatter/resources/test/fixtures/ruff/expression/fstring_py312.py
index 8ce24fa363574..bd1d755f2d5fb 100644
--- a/crates/ruff_python_formatter/resources/test/fixtures/ruff/expression/fstring_py312.py
+++ b/crates/ruff_python_formatter/resources/test/fixtures/ruff/expression/fstring_py312.py
@@ -4,3 +4,14 @@
 
 # Quotes reuse
 f"{'a'}"
+
+# 312+, it's okay to change the outer quotes even when there's a debug expression using the same quotes
+f'foo {10 + len("bar")=}'
+f'''foo {10 + len("""bar""")=}'''
+
+# 312+, it's okay to change the quotes here without creating an invalid f-string
+f'{"""other " """}'
+f'{"""other " """ + "more"}'
+f'{b"""other " """}'
+f'{f"""other " """}'
+
diff --git a/crates/ruff_python_formatter/src/other/f_string.rs b/crates/ruff_python_formatter/src/other/f_string.rs
index 9202ea94aab20..826d5dbf67caf 100644
--- a/crates/ruff_python_formatter/src/other/f_string.rs
+++ b/crates/ruff_python_formatter/src/other/f_string.rs
@@ -1,12 +1,12 @@
+use ruff_formatter::write;
+use ruff_python_ast::{AnyStringFlags, FString, StringFlags};
+use ruff_source_file::Locator;
+
 use crate::prelude::*;
 use crate::preview::{
     is_f_string_formatting_enabled, is_f_string_implicit_concatenated_string_literal_quotes_enabled,
 };
 use crate::string::{Quoting, StringNormalizer, StringQuotes};
-use ruff_formatter::write;
-use ruff_python_ast::{AnyStringFlags, FString, StringFlags};
-use ruff_source_file::Locator;
-use ruff_text_size::Ranged;
 
 use super::f_string_element::FormatFStringElement;
 
@@ -35,7 +35,7 @@ impl Format<PyFormatContext<'_>> for FormatFString<'_> {
         // f-string instead of globally for the entire f-string expression.
         let quoting =
             if is_f_string_implicit_concatenated_string_literal_quotes_enabled(f.context()) {
-                f_string_quoting(self.value, &locator)
+                Quoting::CanChange
             } else {
                 self.quoting
             };
@@ -92,17 +92,21 @@ impl Format<PyFormatContext<'_>> for FormatFString<'_> {
 
 #[derive(Clone, Copy, Debug)]
 pub(crate) struct FStringContext {
-    flags: AnyStringFlags,
+    /// The string flags of the enclosing f-string part.
+    enclosing_flags: AnyStringFlags,
     layout: FStringLayout,
 }
 
 impl FStringContext {
     const fn new(flags: AnyStringFlags, layout: FStringLayout) -> Self {
-        Self { flags, layout }
+        Self {
+            enclosing_flags: flags,
+            layout,
+        }
     }
 
     pub(crate) fn flags(self) -> AnyStringFlags {
-        self.flags
+        self.enclosing_flags
     }
 
     pub(crate) const fn layout(self) -> FStringLayout {
@@ -149,20 +153,3 @@ impl FStringLayout {
         matches!(self, FStringLayout::Multiline)
     }
 }
-
-fn f_string_quoting(f_string: &FString, locator: &Locator) -> Quoting {
-    let triple_quoted = f_string.flags.is_triple_quoted();
-
-    if f_string.elements.expressions().any(|expression| {
-        let string_content = locator.slice(expression.range());
-        if triple_quoted {
-            string_content.contains(r#"""""#) || string_content.contains("'''")
-        } else {
-            string_content.contains(['"', '\''])
-        }
-    }) {
-        Quoting::Preserve
-    } else {
-        Quoting::CanChange
-    }
-}
diff --git a/crates/ruff_python_formatter/src/other/f_string_element.rs b/crates/ruff_python_formatter/src/other/f_string_element.rs
index 12e653e755860..b47a0fa220084 100644
--- a/crates/ruff_python_formatter/src/other/f_string_element.rs
+++ b/crates/ruff_python_formatter/src/other/f_string_element.rs
@@ -2,8 +2,8 @@ use std::borrow::Cow;
 
 use ruff_formatter::{format_args, write, Buffer, RemoveSoftLinesBuffer};
 use ruff_python_ast::{
-    ConversionFlag, Expr, FStringElement, FStringExpressionElement, FStringLiteralElement,
-    StringFlags,
+    AnyStringFlags, ConversionFlag, Expr, FStringElement, FStringExpressionElement,
+    FStringLiteralElement, StringFlags,
 };
 use ruff_text_size::Ranged;
 
@@ -33,7 +33,7 @@ impl Format<PyFormatContext<'_>> for FormatFStringElement<'_> {
     fn fmt(&self, f: &mut PyFormatter) -> FormatResult<()> {
         match self.element {
             FStringElement::Literal(string_literal) => {
-                FormatFStringLiteralElement::new(string_literal, self.context).fmt(f)
+                FormatFStringLiteralElement::new(string_literal, self.context.flags()).fmt(f)
             }
             FStringElement::Expression(expression) => {
                 FormatFStringExpressionElement::new(expression, self.context).fmt(f)
@@ -45,19 +45,23 @@ impl Format<PyFormatContext<'_>> for FormatFStringElement<'_> {
 /// Formats an f-string literal element.
 pub(crate) struct FormatFStringLiteralElement<'a> {
     element: &'a FStringLiteralElement,
-    context: FStringContext,
+    /// Flags of the enclosing F-string part
+    fstring_flags: AnyStringFlags,
 }
 
 impl<'a> FormatFStringLiteralElement<'a> {
-    pub(crate) fn new(element: &'a FStringLiteralElement, context: FStringContext) -> Self {
-        Self { element, context }
+    pub(crate) fn new(element: &'a FStringLiteralElement, fstring_flags: AnyStringFlags) -> Self {
+        Self {
+            element,
+            fstring_flags,
+        }
     }
 }
 
 impl Format<PyFormatContext<'_>> for FormatFStringLiteralElement<'_> {
     fn fmt(&self, f: &mut PyFormatter) -> FormatResult<()> {
         let literal_content = f.context().locator().slice(self.element.range());
-        let normalized = normalize_string(literal_content, 0, self.context.flags(), true);
+        let normalized = normalize_string(literal_content, 0, self.fstring_flags, true);
         match &normalized {
             Cow::Borrowed(_) => source_text_slice(self.element.range()).fmt(f),
             Cow::Owned(normalized) => text(normalized).fmt(f),
diff --git a/crates/ruff_python_formatter/src/preview.rs b/crates/ruff_python_formatter/src/preview.rs
index 92b86f3ccfd7b..bacb9d203f02a 100644
--- a/crates/ruff_python_formatter/src/preview.rs
+++ b/crates/ruff_python_formatter/src/preview.rs
@@ -15,11 +15,13 @@ pub(crate) const fn is_hug_parens_with_braces_and_square_brackets_enabled(
 }
 
 /// Returns `true` if the [`f-string formatting`](https://github.com/astral-sh/ruff/issues/7594) preview style is enabled.
+/// WARNING: This preview style depends on `is_f_string_implicit_concatenated_string_literal_quotes_enabled`.
 pub(crate) fn is_f_string_formatting_enabled(context: &PyFormatContext) -> bool {
     context.is_preview()
 }
 
 /// See [#13539](https://github.com/astral-sh/ruff/pull/13539)
+/// Remove `Quoting` when stabalizing this preview style.
 pub(crate) fn is_f_string_implicit_concatenated_string_literal_quotes_enabled(
     context: &PyFormatContext,
 ) -> bool {
diff --git a/crates/ruff_python_formatter/src/string/normalize.rs b/crates/ruff_python_formatter/src/string/normalize.rs
index 5e5706a38f769..c4913091464f3 100644
--- a/crates/ruff_python_formatter/src/string/normalize.rs
+++ b/crates/ruff_python_formatter/src/string/normalize.rs
@@ -3,7 +3,10 @@ use std::cmp::Ordering;
 use std::iter::FusedIterator;
 
 use ruff_formatter::FormatContext;
-use ruff_python_ast::{str::Quote, AnyStringFlags, StringFlags, StringLikePart};
+use ruff_python_ast::visitor::source_order::SourceOrderVisitor;
+use ruff_python_ast::{
+    str::Quote, AnyStringFlags, BytesLiteral, FString, StringFlags, StringLikePart, StringLiteral,
+};
 use ruff_text_size::{Ranged, TextRange};
 
 use crate::context::FStringState;
@@ -37,53 +40,55 @@ impl<'a, 'src> StringNormalizer<'a, 'src> {
         self
     }
 
-    fn quoting(&self, string: StringLikePart) -> Quoting {
-        match (self.quoting, self.context.f_string_state()) {
-            (Quoting::Preserve, _) => Quoting::Preserve,
-
-            // If we're inside an f-string, we need to make sure to preserve the
-            // existing quotes unless we're inside a triple-quoted f-string and
-            // the inner string itself isn't triple-quoted. For example:
-            //
-            // ```python
-            // f"""outer {"inner"}"""  # Valid
-            // f"""outer {"""inner"""}"""  # Invalid
-            // ```
-            //
-            // Or, if the target version supports PEP 701.
-            //
-            // The reason to preserve the quotes is based on the assumption that
-            // the original f-string is valid in terms of quoting, and we don't
-            // want to change that to make it invalid.
-            (Quoting::CanChange, FStringState::InsideExpressionElement(context)) => {
-                if (context.f_string().flags().is_triple_quoted()
-                    && !string.flags().is_triple_quoted())
-                    || self.context.options().target_version().supports_pep_701()
-                {
-                    Quoting::CanChange
-                } else {
-                    Quoting::Preserve
-                }
-            }
-
-            (Quoting::CanChange, _) => Quoting::CanChange,
-        }
-    }
-
     /// Determines the preferred quote style for `string`.
     /// The formatter should use the preferred quote style unless
     /// it can't because the string contains the preferred quotes OR
     /// it leads to more escaping.
     pub(super) fn preferred_quote_style(&self, string: StringLikePart) -> QuoteStyle {
-        match self.quoting(string) {
+        match self.quoting {
             Quoting::Preserve => QuoteStyle::Preserve,
             Quoting::CanChange => {
                 let preferred_quote_style = self
                     .preferred_quote_style
                     .unwrap_or(self.context.options().quote_style());
 
+                if preferred_quote_style.is_preserve() {
+                    return QuoteStyle::Preserve;
+                }
+
+                // There are two cases where it's necessary to preserve the quotes
+                // if the target version is pre 3.12 and the part is an f-string.
+                if !self.context.options().target_version().supports_pep_701() {
+                    if let StringLikePart::FString(fstring) = string {
+                        // An f-string expression contains a debug text with a quote character
+                        // because the formatter will emit the debug expression **exactly** the same as in the source text.
+                        if is_fstring_with_quoted_debug_expression(fstring, self.context) {
+                            return QuoteStyle::Preserve;
+                        }
+
+                        // An f-string expression that contains a triple quoted string literal expression
+                        // that contains a quote.
+                        if is_fstring_with_triple_quoted_literal_expression_containing_quotes(
+                            fstring,
+                            self.context,
+                        ) {
+                            return QuoteStyle::Preserve;
+                        }
+                    }
+                }
+
+                // For f-strings prefer alternating the quotes unless The outer string is triple quoted and the inner isn't.
+                if let FStringState::InsideExpressionElement(parent_context) =
+                    self.context.f_string_state()
+                {
+                    let parent_flags = parent_context.f_string().flags();
+
+                    if !parent_flags.is_triple_quoted() || string.flags().is_triple_quoted() {
+                        return QuoteStyle::from(parent_flags.quote_style().opposite());
+                    }
+                }
+
                 // Per PEP 8, always prefer double quotes for triple-quoted strings.
-                // Except when using quote-style-preserve.
                 if string.flags().is_triple_quoted() {
                     // ... unless we're formatting a code snippet inside a docstring,
                     // then we specifically want to invert our quote style to avoid
@@ -132,8 +137,6 @@ impl<'a, 'src> StringNormalizer<'a, 'src> {
                     // if it doesn't have perfect alignment with PEP8.
                     if let Some(quote) = self.context.docstring() {
                         QuoteStyle::from(quote.opposite())
-                    } else if preferred_quote_style.is_preserve() {
-                        QuoteStyle::Preserve
                     } else {
                         QuoteStyle::Double
                     }
@@ -163,12 +166,18 @@ impl<'a, 'src> StringNormalizer<'a, 'src> {
             // The preferred quote style is single or double quotes, and the string contains a quote or
             // another character that may require escaping
             (Ok(preferred_quote), Some(first_quote_or_normalized_char_offset)) => {
-                let quote = QuoteMetadata::from_str(
-                    &raw_content[first_quote_or_normalized_char_offset..],
-                    string.flags(),
-                    preferred_quote,
-                )
-                .choose(preferred_quote);
+                let metadata = if string.is_fstring() {
+                    QuoteMetadata::from_part(string, self.context, preferred_quote)
+                } else {
+                    QuoteMetadata::from_str(
+                        &raw_content[first_quote_or_normalized_char_offset..],
+                        string.flags(),
+                        preferred_quote,
+                    )
+                };
+
+                let quote = metadata.choose(preferred_quote);
+
                 string_flags.with_quote_style(quote)
             }
 
@@ -235,6 +244,59 @@ pub(crate) struct QuoteMetadata {
 /// Tracks information about the used quotes in a string which is used
 /// to choose the quotes for a part.
 impl QuoteMetadata {
+    pub(crate) fn from_part(
+        part: StringLikePart,
+        context: &PyFormatContext,
+        preferred_quote: Quote,
+    ) -> Self {
+        match part {
+            StringLikePart::String(_) | StringLikePart::Bytes(_) => {
+                let text = context.locator().slice(part.content_range());
+
+                Self::from_str(text, part.flags(), preferred_quote)
+            }
+            StringLikePart::FString(fstring) => {
+                if is_f_string_formatting_enabled(context) {
+                    // For f-strings, only consider the quotes inside string-literals but ignore
+                    // quotes inside expressions. This allows both the outer and the nested literals
+                    // to make the optimal local-choice to reduce the total number of quotes necessary.
+                    // This doesn't require any pre 312 special handling because an expression
+                    // can never contain the outer quote character, not even escaped:
+                    // ```python
+                    // f"{'escaping a quote like this \" is a syntax error pre 312'}"
+                    // ```
+                    let mut literals = fstring.elements.literals();
+
+                    let Some(first) = literals.next() else {
+                        return QuoteMetadata::from_str("", part.flags(), preferred_quote);
+                    };
+
+                    let mut metadata = QuoteMetadata::from_str(
+                        context.locator().slice(first.range()),
+                        fstring.flags.into(),
+                        preferred_quote,
+                    );
+
+                    for literal in literals {
+                        metadata = metadata
+                            .merge(&QuoteMetadata::from_str(
+                                context.locator().slice(literal.range()),
+                                fstring.flags.into(),
+                                preferred_quote,
+                            ))
+                            .expect("Merge to succeed because all parts have the same flags");
+                    }
+
+                    metadata
+                } else {
+                    let text = context.locator().slice(part.content_range());
+
+                    Self::from_str(text, part.flags(), preferred_quote)
+                }
+            }
+        }
+    }
+
     pub(crate) fn from_str(text: &str, flags: AnyStringFlags, preferred_quote: Quote) -> Self {
         let kind = if flags.is_raw_string() {
             QuoteMetadataKind::raw(text, preferred_quote, flags.is_triple_quoted())
@@ -276,6 +338,61 @@ impl QuoteMetadata {
             },
         }
     }
+
+    /// Merges the quotes metadata of different literals.
+    ///
+    /// ## Raw and triple quoted strings
+    /// Merging raw and triple quoted strings is only correct if all literals are from the same part.
+    /// E.g. it's okay to merge triple and raw strings from a single `FString` part's literals
+    /// but it isn't safe to merge raw and triple quoted strings from different parts of an implicit
+    /// concatenated string. Where safe means, it may lead to incorrect results.
+    pub(super) fn merge(self, other: &QuoteMetadata) -> Option<QuoteMetadata> {
+        let kind = match (self.kind, other.kind) {
+            (
+                QuoteMetadataKind::Regular {
+                    single_quotes: self_single,
+                    double_quotes: self_double,
+                },
+                QuoteMetadataKind::Regular {
+                    single_quotes: other_single,
+                    double_quotes: other_double,
+                },
+            ) => QuoteMetadataKind::Regular {
+                single_quotes: self_single + other_single,
+                double_quotes: self_double + other_double,
+            },
+
+            // Can't merge quotes from raw strings (even when both strings are raw)
+            (
+                QuoteMetadataKind::Raw {
+                    contains_preferred: self_contains_preferred,
+                },
+                QuoteMetadataKind::Raw {
+                    contains_preferred: other_contains_preferred,
+                },
+            ) => QuoteMetadataKind::Raw {
+                contains_preferred: self_contains_preferred || other_contains_preferred,
+            },
+
+            (
+                QuoteMetadataKind::Triple {
+                    contains_preferred: self_contains_preferred,
+                },
+                QuoteMetadataKind::Triple {
+                    contains_preferred: other_contains_preferred,
+                },
+            ) => QuoteMetadataKind::Triple {
+                contains_preferred: self_contains_preferred || other_contains_preferred,
+            },
+
+            (_, _) => return None,
+        };
+
+        Some(Self {
+            kind,
+            source_style: self.source_style,
+        })
+    }
 }
 
 #[derive(Copy, Clone, Debug)]
@@ -738,18 +855,142 @@ impl UnicodeEscape {
     }
 }
 
+/// Returns `true` if `string` is an f-string part that contains a debug expression that uses quotes
+/// and the format target is pre Python 312
+/// We can't join f-strings where:
+///
+/// ```python
+/// f"{10 + len('bar')=}"
+/// f'{10 + len("bar")=}'
+/// f""""{10 + len('''bar''')=}"""
+/// ```
+pub(super) fn is_fstring_with_quoted_debug_expression(
+    fstring: &FString,
+    context: &PyFormatContext,
+) -> bool {
+    if fstring.elements.expressions().any(|expression| {
+        if expression.debug_text.is_some() {
+            let content = context.locator().slice(expression.range());
+            match fstring.flags.quote_style() {
+                Quote::Single => {
+                    if fstring.flags.is_triple_quoted() {
+                        content.contains(r#"""""#)
+                    } else {
+                        content.contains('"')
+                    }
+                }
+                Quote::Double => {
+                    if fstring.flags.is_triple_quoted() {
+                        content.contains("'''")
+                    } else {
+                        content.contains('\'')
+                    }
+                }
+            }
+        } else {
+            false
+        }
+    }) {
+        return true;
+    }
+
+    false
+}
+
+/// Tests if the `fstring` contains any triple quoted string, byte, or f-string literal that
+/// contains a quote character opposite to its own quote character.
+///
+/// ```python
+/// f'{"""other " """}'
+/// ```
+///
+/// We can't flip the quote of the outer f-string because it would result in invalid syntax:
+/// ```python
+/// f"{'''other " '''}'
+/// ```
+pub(super) fn is_fstring_with_triple_quoted_literal_expression_containing_quotes(
+    fstring: &FString,
+    context: &PyFormatContext,
+) -> bool {
+    struct Visitor<'a> {
+        context: &'a PyFormatContext<'a>,
+        found: bool,
+    }
+
+    impl Visitor<'_> {
+        fn visit_string_like_part(&mut self, part: StringLikePart) {
+            if !part.flags().is_triple_quoted() || self.found {
+                return;
+            }
+
+            let contains_quotes = match part {
+                StringLikePart::String(_) | StringLikePart::Bytes(_) => {
+                    self.contains_quote(part.content_range(), part.flags())
+                }
+                StringLikePart::FString(fstring) => {
+                    let mut contains_quotes = false;
+                    for literal in fstring.elements.literals() {
+                        if self.contains_quote(literal.range(), fstring.flags.into()) {
+                            contains_quotes = true;
+                            break;
+                        }
+                    }
+
+                    contains_quotes
+                }
+            };
+
+            if contains_quotes {
+                self.found = true;
+            }
+        }
+
+        fn contains_quote(&self, range: TextRange, flags: AnyStringFlags) -> bool {
+            self.context
+                .locator()
+                .slice(range)
+                .contains(flags.quote_style().as_char())
+        }
+    }
+
+    impl SourceOrderVisitor<'_> for Visitor<'_> {
+        fn visit_f_string(&mut self, f_string: &FString) {
+            self.visit_string_like_part(StringLikePart::FString(f_string));
+        }
+
+        fn visit_string_literal(&mut self, string_literal: &StringLiteral) {
+            self.visit_string_like_part(StringLikePart::String(string_literal));
+        }
+
+        fn visit_bytes_literal(&mut self, bytes_literal: &BytesLiteral) {
+            self.visit_string_like_part(StringLikePart::Bytes(bytes_literal));
+        }
+    }
+
+    let mut visitor = Visitor {
+        context,
+        found: false,
+    };
+
+    ruff_python_ast::visitor::source_order::walk_f_string(&mut visitor, fstring);
+
+    visitor.found
+}
+
 #[cfg(test)]
 mod tests {
     use std::borrow::Cow;
 
-    use super::UnicodeEscape;
-    use crate::string::normalize_string;
     use ruff_python_ast::{
         str::Quote,
         str_prefix::{AnyStringPrefix, ByteStringPrefix},
         AnyStringFlags,
     };
 
+    use crate::string::normalize_string;
+
+    use super::UnicodeEscape;
+
     #[test]
     fn normalize_32_escape() {
         let escape_sequence = UnicodeEscape::new('U', true).unwrap();
diff --git a/crates/ruff_python_formatter/tests/snapshots/black_compatibility@cases__preview_long_strings.py.snap b/crates/ruff_python_formatter/tests/snapshots/black_compatibility@cases__preview_long_strings.py.snap
index eeda12f088cf7..a4c9bc8300142 100644
--- a/crates/ruff_python_formatter/tests/snapshots/black_compatibility@cases__preview_long_strings.py.snap
+++ b/crates/ruff_python_formatter/tests/snapshots/black_compatibility@cases__preview_long_strings.py.snap
@@ -941,7 +941,7 @@ log.info(f"""Skipping: {'a' == 'b'} {desc['ms_name']} {money=} {dte=} {pos_share
  log.info(
 -    "Skipping:"
 -    f" {desc['db_id']} {foo('bar',x=123)} {'foo' != 'bar'} {(x := 'abc=')} {pos_share=} {desc['status']} {desc['exposure_max']}"
-+    f'Skipping: {desc["db_id"]} {foo("bar", x=123)} {"foo" != "bar"} {(x := "abc=")} {pos_share=} {desc["status"]} {desc["exposure_max"]}'
++    f"Skipping: {desc['db_id']} {foo('bar', x=123)} {'foo' != 'bar'} {(x := 'abc=')} {pos_share=} {desc['status']} {desc['exposure_max']}"
  )
  
  log.info(
@@ -965,7 +965,7 @@ log.info(f"""Skipping: {'a' == 'b'} {desc['ms_name']} {money=} {dte=} {pos_share
  log.info(
 -    "Skipping:"
 -    f" {'a' == 'b' == 'c' == 'd'} {desc['ms_name']} {money=} {dte=} {pos_share=} {desc['status']} {desc['exposure_max']}"
-+    f'Skipping: {"a" == "b" == "c" == "d"} {desc["ms_name"]} {money=} {dte=} {pos_share=} {desc["status"]} {desc["exposure_max"]}'
++    f"Skipping: {'a' == 'b' == 'c' == 'd'} {desc['ms_name']} {money=} {dte=} {pos_share=} {desc['status']} {desc['exposure_max']}"
  )
  
  log.info(
@@ -1406,7 +1406,7 @@ log.info(
 )
 
 log.info(
-    f'Skipping: {desc["db_id"]} {foo("bar", x=123)} {"foo" != "bar"} {(x := "abc=")} {pos_share=} {desc["status"]} {desc["exposure_max"]}'
+    f"Skipping: {desc['db_id']} {foo('bar', x=123)} {'foo' != 'bar'} {(x := 'abc=')} {pos_share=} {desc['status']} {desc['exposure_max']}"
 )
 
 log.info(
@@ -1422,7 +1422,7 @@ log.info(
 )
 
 log.info(
-    f'Skipping: {"a" == "b" == "c" == "d"} {desc["ms_name"]} {money=} {dte=} {pos_share=} {desc["status"]} {desc["exposure_max"]}'
+    f"Skipping: {'a' == 'b' == 'c' == 'd'} {desc['ms_name']} {money=} {dte=} {pos_share=} {desc['status']} {desc['exposure_max']}"
 )
 
 log.info(
diff --git a/crates/ruff_python_formatter/tests/snapshots/black_compatibility@cases__preview_long_strings__regression.py.snap b/crates/ruff_python_formatter/tests/snapshots/black_compatibility@cases__preview_long_strings__regression.py.snap
index 54b2c0f438b71..e017e31abfe26 100644
--- a/crates/ruff_python_formatter/tests/snapshots/black_compatibility@cases__preview_long_strings__regression.py.snap
+++ b/crates/ruff_python_formatter/tests/snapshots/black_compatibility@cases__preview_long_strings__regression.py.snap
@@ -1201,10 +1201,10 @@ s = f'Lorem Ipsum is simply dummy text of the printing and typesetting industry:
 +    "With single quote: ' "
 +    f" {my_dict['foo']}"
 +    ' With double quote: " '
-+    f' {my_dict["bar"]}'
++    f" {my_dict['bar']}"
  )
 +
-+s = f'Lorem Ipsum is simply dummy text of the printing and typesetting industry:\'{my_dict["foo"]}\''
++s = f"Lorem Ipsum is simply dummy text of the printing and typesetting industry:'{my_dict['foo']}'"
 ```
 
 ## Ruff Output
@@ -1839,10 +1839,10 @@ s = (
     "With single quote: ' "
     f" {my_dict['foo']}"
     ' With double quote: " '
-    f' {my_dict["bar"]}'
+    f" {my_dict['bar']}"
 )
 
-s = f'Lorem Ipsum is simply dummy text of the printing and typesetting industry:\'{my_dict["foo"]}\''
+s = f"Lorem Ipsum is simply dummy text of the printing and typesetting industry:'{my_dict['foo']}'"
 ```
 
 ## Black Output
diff --git a/crates/ruff_python_formatter/tests/snapshots/format@expression__fstring.py.snap b/crates/ruff_python_formatter/tests/snapshots/format@expression__fstring.py.snap
index 5faebb836e37d..1496a5e98cdc5 100644
--- a/crates/ruff_python_formatter/tests/snapshots/format@expression__fstring.py.snap
+++ b/crates/ruff_python_formatter/tests/snapshots/format@expression__fstring.py.snap
@@ -100,6 +100,8 @@ x = f"aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa { # comment 8
                                              "bbbbbbbbbbbbbbbbbbbbbbbbbbbbb" } ccccccccccccccc"
 x = f"aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa { # comment 9
                                              "bbbbbbbbbbbbbbbbbbbbbbbbbbbbb" = } ccccccccccccccc"
+x = f"aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa { # comment 9
+                                             'bbbbbbbbbbbbbbbbbbbbbbbbbbbbb' = } ccccccccccccccc"
 
 # Multiple larger expressions which exceeds the line length limit. Here, we need to decide
 # whether to split at the first or second expression. This should work similarly to the
@@ -150,18 +152,37 @@ xxxxxxx = f"{
     {'aaaaaaaaaaaaaaaaaaaaaaaaa', 'bbbbbbbbbbbbbbbbbbbbbbbbbbb', 'cccccccccccccccccccccccccc'}
 }"
 
+#############################################################################################
 # Quotes
+#############################################################################################
 f"foo 'bar' {x}"
 f"foo \"bar\" {x}"
 f'foo "bar" {x}'
 f'foo \'bar\' {x}'
 f"foo {"bar"}"
-f"foo {'\'bar\''}"
+
+f"single quoted '{x}' double quoted \"{x}\"" # Same number of quotes => use preferred quote style
+f"single quote ' {x} double quoted \"{x}\""  # More double quotes => use single quotes
+f"single quoted '{x}' double quote \" {x}"  # More single quotes => use double quotes
+
+fr"single quotes ' {x}"  # Keep double because `'` can't be escaped
+fr'double quotes " {x}'  # Keep single because `"` can't be escaped
+fr'flip quotes {x}'  # Use preferred quotes, because raw string contains now quotes.
 
 # Here, the formatter will remove the escapes which is correct because they aren't allowed
 # pre 3.12. This means we can assume that the f-string is used in the context of 3.12.
+f"foo {'\'bar\''}"
 f"foo {'\"bar\"'}"
 
+# Quotes inside the expressions have no impact on the quote selection of the outer string.
+# Required so that the following two examples result in the same formatting.
+f'foo {10 + len("bar")}'
+f"foo {10 + len('bar')}"
+
+# Pre 312, preserve the outer quotes if the f-string contains quotes in the debug expression
+f'foo {10 + len("bar")=}'
+f'''foo {10 + len('''bar''')=}'''
+f'''foo {10 + len('bar')=}'''  # Fine to change the quotes because it uses triple quotes
 
 # Triple-quoted strings
 # It's ok to use the same quote char for the inner string if it's single-quoted.
@@ -170,6 +191,16 @@ f"""test {"inner"}"""
 # But if the inner string is also triple-quoted then we should preserve the existing quotes.
 f"""test {'''inner'''}"""
 
+# It's not okay to change the quote style if the inner string is triple quoted and contains a quote.
+f'{"""other " """}'
+f'{"""other " """ + "more"}'
+f'{b"""other " """}'
+f'{f"""other " """}'
+
+# Not valid Pre 3.12
+f"""test {f'inner {'''inner inner'''}'}"""
+f"""test {f'''inner {"""inner inner"""}'''}"""
+
 # Magic trailing comma
 #
 # The expression formatting will result in breaking it across multiple lines with a
@@ -318,7 +349,7 @@ hello {
 # Implicit concatenated f-string containing quotes
 _ = (
     'This string should change its quotes to double quotes'
-    f'This string uses double quotes in an expression {"woah"}'
+    f'This string uses double quotes in an expression {"it's a quote"}'
     f'This f-string does not use any quotes.'
 )
 ```
@@ -429,13 +460,15 @@ aaaaaaaaaaa = (
 
 # This should never add the optional parentheses because even after adding them, the
 # f-string exceeds the line length limit.
-x = f"aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa {"bbbbbbbbbbbbbbbbbbbbbbbbbbbbb"} ccccccccccccccc"
+x = f"aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa {'bbbbbbbbbbbbbbbbbbbbbbbbbbbbb'} ccccccccccccccc"
 x = f"aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa { "bbbbbbbbbbbbbbbbbbbbbbbbbbbbb" = } ccccccccccccccc"
 x = f"aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa {  # comment 8
-    "bbbbbbbbbbbbbbbbbbbbbbbbbbbbb"
+    'bbbbbbbbbbbbbbbbbbbbbbbbbbbbb'
 } ccccccccccccccc"
 x = f"aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa { # comment 9
                                              "bbbbbbbbbbbbbbbbbbbbbbbbbbbbb" = } ccccccccccccccc"
+x = f"aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa { # comment 9
+                                             'bbbbbbbbbbbbbbbbbbbbbbbbbbbbb' = } ccccccccccccccc"
 
 # Multiple larger expressions which exceeds the line length limit. Here, we need to decide
 # whether to split at the first or second expression. This should work similarly to the
@@ -496,18 +529,37 @@ xxxxxxx = f"{
     }
 }"
 
+#############################################################################################
 # Quotes
+#############################################################################################
 f"foo 'bar' {x}"
 f'foo "bar" {x}'
 f'foo "bar" {x}'
 f"foo 'bar' {x}"
-f"foo {"bar"}"
-f"foo {'\'bar\''}"
+f"foo {'bar'}"
+
+f"single quoted '{x}' double quoted \"{x}\""  # Same number of quotes => use preferred quote style
+f'single quote \' {x} double quoted "{x}"'  # More double quotes => use single quotes
+f"single quoted '{x}' double quote \" {x}"  # More single quotes => use double quotes
+
+rf"single quotes ' {x}"  # Keep double because `'` can't be escaped
+rf'double quotes " {x}'  # Keep single because `"` can't be escaped
+rf"flip quotes {x}"  # Use preferred quotes, because raw string contains now quotes.
 
 # Here, the formatter will remove the escapes which is correct because they aren't allowed
 # pre 3.12. This means we can assume that the f-string is used in the context of 3.12.
+f"foo {"'bar'"}"
 f"foo {'"bar"'}"
 
+# Quotes inside the expressions have no impact on the quote selection of the outer string.
+# Required so that the following two examples result in the same formatting.
+f"foo {10 + len('bar')}"
+f"foo {10 + len('bar')}"
+
+# Pre 312, preserve the outer quotes if the f-string contains quotes in the debug expression
+f'foo {10 + len("bar")=}'
+f"""foo {10 + len('''bar''')=}"""
+f"""foo {10 + len('bar')=}"""  # Fine to change the quotes because it uses triple quotes
 
 # Triple-quoted strings
 # It's ok to use the same quote char for the inner string if it's single-quoted.
@@ -516,6 +568,16 @@ f"""test {"inner"}"""
 # But if the inner string is also triple-quoted then we should preserve the existing quotes.
 f"""test {'''inner'''}"""
 
+# It's not okay to change the quote style if the inner string is triple quoted and contains a quote.
+f'{"""other " """}'
+f'{"""other " """ + "more"}'
+f'{b"""other " """}'
+f'{f"""other " """}'
+
+# Not valid Pre 3.12
+f"""test {f"inner {'''inner inner'''}"}"""
+f"""test {f'''inner {"""inner inner"""}'''}"""
+
 # Magic trailing comma
 #
 # The expression formatting will result in breaking it across multiple lines with a
@@ -662,7 +724,7 @@ hello {
 # Implicit concatenated f-string containing quotes
 _ = (
     "This string should change its quotes to double quotes"
-    f'This string uses double quotes in an expression {"woah"}'
+    f"This string uses double quotes in an expression {"it's a quote"}"
     f"This f-string does not use any quotes."
 )
 ```
@@ -778,6 +840,8 @@ x = f"aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa { # comment 8
                                              "bbbbbbbbbbbbbbbbbbbbbbbbbbbbb" } ccccccccccccccc"
 x = f"aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa { # comment 9
                                              "bbbbbbbbbbbbbbbbbbbbbbbbbbbbb" = } ccccccccccccccc"
+x = f"aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa { # comment 9
+                                             'bbbbbbbbbbbbbbbbbbbbbbbbbbbbb' = } ccccccccccccccc"
 
 # Multiple larger expressions which exceeds the line length limit. Here, we need to decide
 # whether to split at the first or second expression. This should work similarly to the
@@ -828,18 +892,37 @@ xxxxxxx = f"{
     {'aaaaaaaaaaaaaaaaaaaaaaaaa', 'bbbbbbbbbbbbbbbbbbbbbbbbbbb', 'cccccccccccccccccccccccccc'}
 }"
 
+#############################################################################################
 # Quotes
+#############################################################################################
 f"foo 'bar' {x}"
 f'foo "bar" {x}'
 f'foo "bar" {x}'
 f"foo 'bar' {x}"
 f"foo {"bar"}"
-f"foo {'\'bar\''}"
+
+f"single quoted '{x}' double quoted \"{x}\""  # Same number of quotes => use preferred quote style
+f'single quote \' {x} double quoted "{x}"'  # More double quotes => use single quotes
+f"single quoted '{x}' double quote \" {x}"  # More single quotes => use double quotes
+
+rf"single quotes ' {x}"  # Keep double because `'` can't be escaped
+rf'double quotes " {x}'  # Keep single because `"` can't be escaped
+rf"flip quotes {x}"  # Use preferred quotes, because raw string contains now quotes.
 
 # Here, the formatter will remove the escapes which is correct because they aren't allowed
 # pre 3.12. This means we can assume that the f-string is used in the context of 3.12.
+f"foo {'\'bar\''}"
 f"foo {'\"bar\"'}"
 
+# Quotes inside the expressions have no impact on the quote selection of the outer string.
+# Required so that the following two examples result in the same formatting.
+f'foo {10 + len("bar")}'
+f"foo {10 + len('bar')}"
+
+# Pre 312, preserve the outer quotes if the f-string contains quotes in the debug expression
+f'foo {10 + len("bar")=}'
+f'''foo {10 + len('''bar''')=}'''
+f"""foo {10 + len('bar')=}"""  # Fine to change the quotes because it uses triple quotes
 
 # Triple-quoted strings
 # It's ok to use the same quote char for the inner string if it's single-quoted.
@@ -848,6 +931,16 @@ f"""test {"inner"}"""
 # But if the inner string is also triple-quoted then we should preserve the existing quotes.
 f"""test {'''inner'''}"""
 
+# It's not okay to change the quote style if the inner string is triple quoted and contains a quote.
+f'{"""other " """}'
+f'{"""other " """ + "more"}'
+f'{b"""other " """}'
+f'{f"""other " """}'
+
+# Not valid Pre 3.12
+f"""test {f'inner {'''inner inner'''}'}"""
+f"""test {f'''inner {"""inner inner"""}'''}"""
+
 # Magic trailing comma
 #
 # The expression formatting will result in breaking it across multiple lines with a
@@ -994,7 +1087,7 @@ hello {
 # Implicit concatenated f-string containing quotes
 _ = (
     'This string should change its quotes to double quotes'
-    f'This string uses double quotes in an expression {"woah"}'
+    f'This string uses double quotes in an expression {"it's a quote"}'
     f'This f-string does not use any quotes.'
 )
 ```
@@ -1022,7 +1115,7 @@ _ = (
      "    f()\n"
      # XXX: The following line changes depending on whether the tests
      # are run through the interactive interpreter or with -m
-@@ -67,64 +67,72 @@
+@@ -67,29 +67,31 @@
  x = f"{a}"
  x = f"{
      a = }"
@@ -1052,16 +1145,17 @@ _ = (
  # This should never add the optional parentheses because even after adding them, the
  # f-string exceeds the line length limit.
 -x = f"aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa { "bbbbbbbbbbbbbbbbbbbbbbbbbbbbb" } ccccccccccccccc"
-+x = f"aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa {"bbbbbbbbbbbbbbbbbbbbbbbbbbbbb"} ccccccccccccccc"
++x = f"aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa {'bbbbbbbbbbbbbbbbbbbbbbbbbbbbb'} ccccccccccccccc"
  x = f"aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa { "bbbbbbbbbbbbbbbbbbbbbbbbbbbbb" = } ccccccccccccccc"
 -x = f"aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa { # comment 8
 -                                             "bbbbbbbbbbbbbbbbbbbbbbbbbbbbb" } ccccccccccccccc"
 +x = f"aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa {  # comment 8
-+    "bbbbbbbbbbbbbbbbbbbbbbbbbbbbb"
++    'bbbbbbbbbbbbbbbbbbbbbbbbbbbbb'
 +} ccccccccccccccc"
  x = f"aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa { # comment 9
                                               "bbbbbbbbbbbbbbbbbbbbbbbbbbbbb" = } ccccccccccccccc"
- 
+ x = f"aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa { # comment 9
+@@ -98,35 +100,41 @@
  # Multiple larger expressions which exceeds the line length limit. Here, we need to decide
  # whether to split at the first or second expression. This should work similarly to the
  # assignment statement formatting where we split from right to left in preview mode.
@@ -1119,7 +1213,7 @@ _ = (
  x = f"{    # comment 13
      {'x': 1, 'y': 2} = }"
  # But, if there's a format specifier or a conversion flag then we don't need to add
-@@ -139,7 +147,11 @@
+@@ -141,7 +149,11 @@
  }"
  # And, split the expression itself because it exceeds the line length.
  xxxxxxx = f"{
@@ -1131,14 +1225,36 @@ _ = (
 +    }
  }"
  
- # Quotes
-@@ -152,13 +164,13 @@
+ #############################################################################################
+@@ -151,7 +163,7 @@
+ f'foo "bar" {x}'
+ f'foo "bar" {x}'
+ f"foo 'bar' {x}"
+-f"foo {"bar"}"
++f"foo {'bar'}"
+ 
+ f"single quoted '{x}' double quoted \"{x}\""  # Same number of quotes => use preferred quote style
+ f'single quote \' {x} double quoted "{x}"'  # More double quotes => use single quotes
+@@ -163,23 +175,23 @@
  
  # Here, the formatter will remove the escapes which is correct because they aren't allowed
  # pre 3.12. This means we can assume that the f-string is used in the context of 3.12.
+-f"foo {'\'bar\''}"
 -f"foo {'\"bar\"'}"
++f"foo {"'bar'"}"
 +f"foo {'"bar"'}"
  
+ # Quotes inside the expressions have no impact on the quote selection of the outer string.
+ # Required so that the following two examples result in the same formatting.
+-f'foo {10 + len("bar")}'
+ f"foo {10 + len('bar')}"
++f"foo {10 + len('bar')}"
+ 
+ # Pre 312, preserve the outer quotes if the f-string contains quotes in the debug expression
+ f'foo {10 + len("bar")=}'
+-f'''foo {10 + len('''bar''')=}'''
++f"""foo {10 + len('''bar''')=}"""
+ f"""foo {10 + len('bar')=}"""  # Fine to change the quotes because it uses triple quotes
  
  # Triple-quoted strings
  # It's ok to use the same quote char for the inner string if it's single-quoted.
@@ -1148,7 +1264,16 @@ _ = (
  # But if the inner string is also triple-quoted then we should preserve the existing quotes.
  f"""test {'''inner'''}"""
  
-@@ -171,63 +183,66 @@
+@@ -190,7 +202,7 @@
+ f'{f"""other " """}'
+ 
+ # Not valid Pre 3.12
+-f"""test {f'inner {'''inner inner'''}'}"""
++f"""test {f"inner {'''inner inner'''}"}"""
+ f"""test {f'''inner {"""inner inner"""}'''}"""
+ 
+ # Magic trailing comma
+@@ -202,63 +214,66 @@
  f"aaaaaaa {['aaaaaaaaaaaaaaa', 'bbbbbbbbbbbbb', 'ccccccccccccccccc', 'ddddddddddddddd', 'eeeeeeeeeeeeee']} aaaaaaa"
  
  # And, if the trailing comma is already present, we still need to remove it.
@@ -1243,7 +1368,7 @@ _ = (
       # comment} cccccccccc"""
  
  # Conversion flags
-@@ -235,24 +250,21 @@
+@@ -266,24 +281,21 @@
  # This is not a valid Python code because of the additional whitespace between the `!`
  # and conversion type. But, our parser isn't strict about this. This should probably be
  # removed once we have a strict parser.
@@ -1275,7 +1400,7 @@ _ = (
  
  x = f"""
  {              # comment 22
-@@ -261,19 +273,19 @@
+@@ -292,19 +304,19 @@
  
  # Here, the debug expression is in a nested f-string so we should start preserving
  # whitespaces from that point onwards. This means we should format the outer f-string.
@@ -1303,7 +1428,7 @@ _ = (
      # comment 27
      # comment 28
  } woah {x}"
-@@ -287,27 +299,27 @@
+@@ -318,27 +330,27 @@
          if indent2:
              foo = f"""hello world
  hello {
@@ -1343,9 +1468,10 @@ _ = (
  # Implicit concatenated f-string containing quotes
  _ = (
 -    'This string should change its quotes to double quotes'
-+    "This string should change its quotes to double quotes"
-     f'This string uses double quotes in an expression {"woah"}'
+-    f'This string uses double quotes in an expression {"it's a quote"}'
 -    f'This f-string does not use any quotes.'
++    "This string should change its quotes to double quotes"
++    f"This string uses double quotes in an expression {"it's a quote"}"
 +    f"This f-string does not use any quotes."
  )
 ```
diff --git a/crates/ruff_python_formatter/tests/snapshots/format@expression__fstring_py312.py.snap b/crates/ruff_python_formatter/tests/snapshots/format@expression__fstring_py312.py.snap
index fd22501c96a68..75b2a13bdc59e 100644
--- a/crates/ruff_python_formatter/tests/snapshots/format@expression__fstring_py312.py.snap
+++ b/crates/ruff_python_formatter/tests/snapshots/format@expression__fstring_py312.py.snap
@@ -10,6 +10,17 @@ input_file: crates/ruff_python_formatter/resources/test/fixtures/ruff/expression
 
 # Quotes reuse
 f"{'a'}"
+
+# 312+, it's okay to change the outer quotes even when there's a debug expression using the same quotes
+f'foo {10 + len("bar")=}'
+f'''foo {10 + len("""bar""")=}'''
+
+# 312+, it's okay to change the quotes here without creating an invalid f-string
+f'{"""other " """}'
+f'{"""other " """ + "more"}'
+f'{b"""other " """}'
+f'{f"""other " """}'
+
 ```
 
 ## Outputs
@@ -35,6 +46,16 @@ source_type                = Python
 
 # Quotes reuse
 f"{'a'}"
+
+# 312+, it's okay to change the outer quotes even when there's a debug expression using the same quotes
+f'foo {10 + len("bar")=}'
+f'''foo {10 + len("""bar""")=}'''
+
+# 312+, it's okay to change the quotes here without creating an invalid f-string
+f'{"""other " """}'
+f'{"""other " """ + "more"}'
+f'{b"""other " """}'
+f'{f"""other " """}'
 ```
 
 
@@ -42,10 +63,22 @@ f"{'a'}"
 ```diff
 --- Stable
 +++ Preview
-@@ -3,4 +3,4 @@
- # version isn't set.
+@@ -6,11 +6,11 @@
+ f"{'a'}"
+ 
+ # 312+, it's okay to change the outer quotes even when there's a debug expression using the same quotes
+-f'foo {10 + len("bar")=}'
+-f'''foo {10 + len("""bar""")=}'''
++f"foo {10 + len("bar")=}"
++f"""foo {10 + len("""bar""")=}"""
  
- # Quotes reuse
--f"{'a'}"
-+f"{"a"}"
+ # 312+, it's okay to change the quotes here without creating an invalid f-string
+-f'{"""other " """}'
+-f'{"""other " """ + "more"}'
+-f'{b"""other " """}'
+-f'{f"""other " """}'
++f"{'''other " '''}"
++f"{'''other " ''' + 'more'}"
++f"{b'''other " '''}"
++f"{f'''other " '''}"
 ```