diff --git a/crates/ruff_python_formatter/resources/test/fixtures/ruff/expression/string.py b/crates/ruff_python_formatter/resources/test/fixtures/ruff/expression/string.py
index 6767a2463e9ed..78e215f91ada6 100644
--- a/crates/ruff_python_formatter/resources/test/fixtures/ruff/expression/string.py
+++ b/crates/ruff_python_formatter/resources/test/fixtures/ruff/expression/string.py
@@ -24,6 +24,12 @@
 r"Test"
 R"Test"
 
+# Block conversion if there is an unescaped quote just before the end of the triple
+# quoted string
+r'''\""'''
+r'''""'''
+r'\""'
+
 'This string will not include \
 backslashes or newline characters.'
 
diff --git a/crates/ruff_python_formatter/src/expression/string.rs b/crates/ruff_python_formatter/src/expression/string.rs
index fdf6270982562..d6ed59f5ed8e5 100644
--- a/crates/ruff_python_formatter/src/expression/string.rs
+++ b/crates/ruff_python_formatter/src/expression/string.rs
@@ -323,14 +323,21 @@ fn preferred_quotes_raw(
                     break true;
                 }
 
-                if chars.peek() == Some(&configured_quote_char) {
-                    // `""` or `''`
-                    chars.next();
+                match chars.peek() {
+                    // We can't turn `r'''\""'''` into `r"""\"""""`, this would confuse the parser
+                    // about where the closing triple quotes start
+                    None => break true,
+                    Some(next) if *next == configured_quote_char => {
+                        // `""` or `''`
+                        chars.next();
 
-                    if chars.peek() == Some(&configured_quote_char) {
-                        // `"""` or `'''`
-                        break true;
+                        // We can't turn `r'''""'''` into `r""""""""`, nor can we have
+                        // `"""` or `'''` respectively inside the string
+                        if chars.peek().is_none() || chars.peek() == Some(&configured_quote_char) {
+                            break true;
+                        }
                     }
+                    _ => {}
                 }
             }
             Some(_) => continue,
diff --git a/crates/ruff_python_formatter/tests/snapshots/format@expression__string.py.snap b/crates/ruff_python_formatter/tests/snapshots/format@expression__string.py.snap
index 53afe8b2a34c0..a3ed8ac6ec4b0 100644
--- a/crates/ruff_python_formatter/tests/snapshots/format@expression__string.py.snap
+++ b/crates/ruff_python_formatter/tests/snapshots/format@expression__string.py.snap
@@ -30,6 +30,12 @@ U"Test"
 r"Test"
 R"Test"
 
+# Block conversion if there is an unescaped quote just before the end of the triple
+# quoted string
+r'''\""'''
+r'''""'''
+r'\""'
+
 'This string will not include \
 backslashes or newline characters.'
 
@@ -162,6 +168,12 @@ magic-trailing-comma    = Respect
 r"Test"
 R"Test"
 
+# Block conversion if there is an unescaped quote just before the end of the triple
+# quoted string
+r'''\""'''
+r'''""'''
+r'\""'
+
 "This string will not include \
 backslashes or newline characters."
 
@@ -310,6 +322,12 @@ magic-trailing-comma    = Respect
 r'Test'
 R'Test'
 
+# Block conversion if there is an unescaped quote just before the end of the triple
+# quoted string
+r'''\""'''
+r'''""'''
+r'\""'
+
 'This string will not include \
 backslashes or newline characters.'