diff --git a/crates/ruff_linter/resources/test/fixtures/pycodestyle/E2_syntax_error.py b/crates/ruff_linter/resources/test/fixtures/pycodestyle/E2_syntax_error.py
new file mode 100644
index 0000000000000..34c9579d58cc2
--- /dev/null
+++ b/crates/ruff_linter/resources/test/fixtures/pycodestyle/E2_syntax_error.py
@@ -0,0 +1 @@
+a = (1 or)
diff --git a/crates/ruff_linter/src/rules/pycodestyle/mod.rs b/crates/ruff_linter/src/rules/pycodestyle/mod.rs
index a6d850f862aef..156fde4924b48 100644
--- a/crates/ruff_linter/src/rules/pycodestyle/mod.rs
+++ b/crates/ruff_linter/src/rules/pycodestyle/mod.rs
@@ -148,6 +148,23 @@ mod tests {
         Ok(())
     }
 
+    /// Tests the compatibility of E2 rules (E202, E225 and E275) on syntactically incorrect code.
+    #[test]
+    fn white_space_syntax_error_compatibility() -> Result<()> {
+        let diagnostics = test_path(
+            Path::new("pycodestyle").join("E2_syntax_error.py"),
+            &settings::LinterSettings {
+                ..settings::LinterSettings::for_rules([
+                    Rule::MissingWhitespaceAroundOperator,
+                    Rule::MissingWhitespaceAfterKeyword,
+                    Rule::WhitespaceBeforeCloseBracket,
+                ])
+            },
+        )?;
+        assert_messages!(diagnostics);
+        Ok(())
+    }
+
     #[test_case(Rule::BlankLineBetweenMethods, Path::new("E30.py"))]
     #[test_case(Rule::BlankLinesTopLevel, Path::new("E30.py"))]
     #[test_case(Rule::TooManyBlankLines, Path::new("E30.py"))]
diff --git a/crates/ruff_linter/src/rules/pycodestyle/rules/logical_lines/missing_whitespace_after_keyword.rs b/crates/ruff_linter/src/rules/pycodestyle/rules/logical_lines/missing_whitespace_after_keyword.rs
index 7aa8cfc24764a..296d9514bda6e 100644
--- a/crates/ruff_linter/src/rules/pycodestyle/rules/logical_lines/missing_whitespace_after_keyword.rs
+++ b/crates/ruff_linter/src/rules/pycodestyle/rules/logical_lines/missing_whitespace_after_keyword.rs
@@ -59,7 +59,13 @@ pub(crate) fn missing_whitespace_after_keyword(
                 || tok0_kind == TokenKind::Yield && tok1_kind == TokenKind::Rpar
                 || matches!(
                     tok1_kind,
-                    TokenKind::Colon | TokenKind::Newline | TokenKind::NonLogicalNewline
+                    TokenKind::Colon
+                        | TokenKind::Newline
+                        | TokenKind::NonLogicalNewline
+                        // In the event of a syntax error, do not attempt to add a whitespace.
+                        | TokenKind::Rpar
+                        | TokenKind::Rsqb
+                        | TokenKind::Rbrace
                 ))
             && tok0.end() == tok1.start()
         {
diff --git a/crates/ruff_linter/src/rules/pycodestyle/rules/logical_lines/missing_whitespace_around_operator.rs b/crates/ruff_linter/src/rules/pycodestyle/rules/logical_lines/missing_whitespace_around_operator.rs
index c5432802ccd26..fd182648caec3 100644
--- a/crates/ruff_linter/src/rules/pycodestyle/rules/logical_lines/missing_whitespace_around_operator.rs
+++ b/crates/ruff_linter/src/rules/pycodestyle/rules/logical_lines/missing_whitespace_around_operator.rs
@@ -211,6 +211,21 @@ pub(crate) fn missing_whitespace_around_operator(
             } else {
                 NeedsSpace::No
             }
+        } else if tokens.peek().is_some_and(|token| {
+            matches!(
+                token.kind(),
+                TokenKind::Rpar | TokenKind::Rsqb | TokenKind::Rbrace
+            )
+        }) {
+            // There should not be a closing bracket directly after a token, as it is a syntax
+            // error. For example:
+            // ```
+            // 1+)
+            // ```
+            //
+            // However, allow it in order to prevent entering an infinite loop in which E225 adds a
+            // space only for E202 to remove it.
+            NeedsSpace::No
         } else if is_whitespace_needed(kind) {
             NeedsSpace::Yes
         } else {
diff --git a/crates/ruff_linter/src/rules/pycodestyle/snapshots/ruff_linter__rules__pycodestyle__tests__white_space_syntax_error_compatibility.snap b/crates/ruff_linter/src/rules/pycodestyle/snapshots/ruff_linter__rules__pycodestyle__tests__white_space_syntax_error_compatibility.snap
new file mode 100644
index 0000000000000..6dcc4546f11f9
--- /dev/null
+++ b/crates/ruff_linter/src/rules/pycodestyle/snapshots/ruff_linter__rules__pycodestyle__tests__white_space_syntax_error_compatibility.snap
@@ -0,0 +1,4 @@
+---
+source: crates/ruff_linter/src/rules/pycodestyle/mod.rs
+---
+