diff --git a/README.md b/README.md
index f3ec7dbeeb6ce5..6ff48b2a121744 100644
--- a/README.md
+++ b/README.md
@@ -1741,6 +1741,24 @@ cache-dir = "~/.cache/ruff"
 
 ---
 
+#### [`comment-tags`](#comment-tags)
+
+A list of comment tags to recognize (e.g. TODO, FIXME, XXX).
+Comments starting with these tags will be skipped by E501 and ERA001.
+
+**Default value**: `["TODO", "FIXME", "XXX"]`
+
+**Type**: `Vec<String>`
+
+**Example usage**:
+
+```toml
+[tool.ruff]
+comment-tags = ["TODO", "FIXME", "HACK"]
+```
+
+---
+
 #### [`dummy-variable-rgx`](#dummy-variable-rgx)
 
 A regular expression used to identify "dummy" variables, or those which
@@ -2953,6 +2971,26 @@ staticmethod-decorators = ["staticmethod", "stcmthd"]
 
 ---
 
+### `pycodestyle`
+
+#### [`allow-overlong-lines-for-comment-tags`](#allow-overlong-lines-for-comment-tags)
+
+Whether or not E501 (LineTooLong) should be triggered for comments
+starting with one of the `comment-tags`.
+
+**Default value**: `false`
+
+**Type**: `bool`
+
+**Example usage**:
+
+```toml
+[tool.ruff.pycodestyle]
+allow-overlong-lines-for-comment-tags = true
+```
+
+---
+
 ### `pydocstyle`
 
 #### [`convention`](#convention)
diff --git a/flake8_to_ruff/src/converter.rs b/flake8_to_ruff/src/converter.rs
index 53498c7234cf34..9cfb27af784323 100644
--- a/flake8_to_ruff/src/converter.rs
+++ b/flake8_to_ruff/src/converter.rs
@@ -397,6 +397,7 @@ mod tests {
             src: None,
             target_version: None,
             unfixable: None,
+            comment_tags: None,
             update_check: None,
             flake8_annotations: None,
             flake8_bugbear: None,
@@ -409,6 +410,7 @@ mod tests {
             isort: None,
             mccabe: None,
             pep8_naming: None,
+            pycodestyle: None,
             pydocstyle: None,
             pyupgrade: None,
         });
@@ -457,6 +459,7 @@ mod tests {
             src: None,
             target_version: None,
             unfixable: None,
+            comment_tags: None,
             update_check: None,
             flake8_annotations: None,
             flake8_bugbear: None,
@@ -469,6 +472,7 @@ mod tests {
             isort: None,
             mccabe: None,
             pep8_naming: None,
+            pycodestyle: None,
             pydocstyle: None,
             pyupgrade: None,
         });
@@ -517,6 +521,7 @@ mod tests {
             src: None,
             target_version: None,
             unfixable: None,
+            comment_tags: None,
             update_check: None,
             flake8_annotations: None,
             flake8_bugbear: None,
@@ -529,6 +534,7 @@ mod tests {
             isort: None,
             mccabe: None,
             pep8_naming: None,
+            pycodestyle: None,
             pydocstyle: None,
             pyupgrade: None,
         });
@@ -577,6 +583,7 @@ mod tests {
             src: None,
             target_version: None,
             unfixable: None,
+            comment_tags: None,
             update_check: None,
             flake8_annotations: None,
             flake8_bugbear: None,
@@ -589,6 +596,7 @@ mod tests {
             isort: None,
             mccabe: None,
             pep8_naming: None,
+            pycodestyle: None,
             pydocstyle: None,
             pyupgrade: None,
         });
@@ -637,6 +645,7 @@ mod tests {
             src: None,
             target_version: None,
             unfixable: None,
+            comment_tags: None,
             update_check: None,
             flake8_annotations: None,
             flake8_bugbear: None,
@@ -654,6 +663,7 @@ mod tests {
             isort: None,
             mccabe: None,
             pep8_naming: None,
+            pycodestyle: None,
             pydocstyle: None,
             pyupgrade: None,
         });
@@ -705,6 +715,7 @@ mod tests {
             src: None,
             target_version: None,
             unfixable: None,
+            comment_tags: None,
             update_check: None,
             flake8_annotations: None,
             flake8_bugbear: None,
@@ -717,6 +728,7 @@ mod tests {
             isort: None,
             mccabe: None,
             pep8_naming: None,
+            pycodestyle: None,
             pydocstyle: Some(pydocstyle::settings::Options {
                 convention: Some(Convention::Numpy),
             }),
@@ -768,6 +780,7 @@ mod tests {
             src: None,
             target_version: None,
             unfixable: None,
+            comment_tags: None,
             update_check: None,
             flake8_annotations: None,
             flake8_bugbear: None,
@@ -785,6 +798,7 @@ mod tests {
             isort: None,
             mccabe: None,
             pep8_naming: None,
+            pycodestyle: None,
             pydocstyle: None,
             pyupgrade: None,
         });
diff --git a/resources/test/fixtures/pycodestyle/E501_1.py b/resources/test/fixtures/pycodestyle/E501_1.py
new file mode 100644
index 00000000000000..9298ce38daebd5
--- /dev/null
+++ b/resources/test/fixtures/pycodestyle/E501_1.py
@@ -0,0 +1,6 @@
+# TODO: comments starting with one of the configured comment-tags sometimes are longer than line-length so that you can easily find them with `git grep`
+# TODO comments starting with one of the configured comment-tags sometimes are longer than line-length so that you can easily find them with `git grep`
+#     TODO    comments starting with one of the configured comment-tags sometimes are longer than line-length so that you can easily find them with `git grep`
+# FIXME: comments starting with one of the configured comment-tags sometimes are longer than line-length so that you can easily find them with `git grep`
+# FIXME comments starting with one of the configured comment-tags sometimes are longer than line-length so that you can easily find them with `git grep`
+#     FIXME    comments starting with one of the configured comment-tags sometimes are longer than line-length so that you can easily find them with `git grep`
diff --git a/ruff.schema.json b/ruff.schema.json
index 0e7d1321808164..4a12d94b6b8a4d 100644
--- a/ruff.schema.json
+++ b/ruff.schema.json
@@ -22,6 +22,16 @@
         "null"
       ]
     },
+    "comment-tags": {
+      "description": "A list of comment tags to recognize (e.g. TODO, FIXME, XXX). Comments starting with these tags will be skipped by E501 and ERA001.",
+      "type": [
+        "array",
+        "null"
+      ],
+      "items": {
+        "type": "string"
+      }
+    },
     "dummy-variable-rgx": {
       "description": "A regular expression used to identify \"dummy\" variables, or those which should be ignored when evaluating (e.g.) unused-variable checks. The default expression matches `_`, `__`, and `_var`, but not `_var_`.",
       "type": [
@@ -288,6 +298,17 @@
         }
       }
     },
+    "pycodestyle": {
+      "description": "Options for the `pycodestyle` plugin.",
+      "anyOf": [
+        {
+          "$ref": "#/definitions/Pycodestyle"
+        },
+        {
+          "type": "null"
+        }
+      ]
+    },
     "pydocstyle": {
       "description": "Options for the `pydocstyle` plugin.",
       "anyOf": [
@@ -1418,6 +1439,19 @@
       },
       "additionalProperties": false
     },
+    "Pycodestyle": {
+      "type": "object",
+      "properties": {
+        "allow-overlong-lines-for-comment-tags": {
+          "description": "Whether or not E501 (LineTooLong) should be triggered for comments starting with one of the `comment-tags`.",
+          "type": [
+            "boolean",
+            "null"
+          ]
+        }
+      },
+      "additionalProperties": false
+    },
     "Pydocstyle": {
       "type": "object",
       "properties": {
diff --git a/src/checkers/lines.rs b/src/checkers/lines.rs
index 2d244ef9327953..6cd8d5397fa35c 100644
--- a/src/checkers/lines.rs
+++ b/src/checkers/lines.rs
@@ -57,7 +57,7 @@ pub fn check_lines(
         }
 
         if enforce_line_too_long {
-            if let Some(check) = line_too_long(index, line, settings.line_length) {
+            if let Some(check) = line_too_long(index, line, settings) {
                 checks.push(check);
             }
         }
diff --git a/src/eradicate/checks.rs b/src/eradicate/checks.rs
index 5cefb29b3a6e8b..cbfda5873c9120 100644
--- a/src/eradicate/checks.rs
+++ b/src/eradicate/checks.rs
@@ -31,7 +31,7 @@ pub fn commented_out_code(
     let line = locator.slice_source_code_range(&Range::new(location, end_location));
 
     // Verify that the comment is on its own line, and that it contains code.
-    if is_standalone_comment(&line) && comment_contains_code(&line) {
+    if is_standalone_comment(&line) && comment_contains_code(&line, &settings.comment_tags[..]) {
         let mut check = Check::new(CheckKind::CommentedOutCode, Range::new(start, end));
         if matches!(autofix, flags::Autofix::Enabled)
             && settings.fixable.contains(&CheckCode::ERA001)
diff --git a/src/eradicate/detection.rs b/src/eradicate/detection.rs
index 4d368f9800cad5..1c39bf960cc8ce 100644
--- a/src/eradicate/detection.rs
+++ b/src/eradicate/detection.rs
@@ -4,7 +4,7 @@ use regex::Regex;
 
 static ALLOWLIST_REGEX: Lazy<Regex> = Lazy::new(|| {
     Regex::new(
-        r"^(?i)(?:pylint|pyright|noqa|nosec|type:\s*ignore|fmt:\s*(on|off)|isort:\s*(on|off|skip|skip_file|split|dont-add-imports(:\s*\[.*?])?)|TODO|FIXME|XXX)"
+        r"^(?i)(?:pylint|pyright|noqa|nosec|type:\s*ignore|fmt:\s*(on|off)|isort:\s*(on|off|skip|skip_file|split|dont-add-imports(:\s*\[.*?])?))"
     ).unwrap()
 });
 static BRACKET_REGEX: Lazy<Regex> = Lazy::new(|| Regex::new(r"^[()\[\]{}\s]+$").unwrap());
@@ -30,7 +30,7 @@ static PARTIAL_DICTIONARY_REGEX: Lazy<Regex> =
 static PRINT_RETURN_REGEX: Lazy<Regex> = Lazy::new(|| Regex::new(r"^(print|return)\b\s*").unwrap());
 
 /// Returns `true` if a comment contains Python code.
-pub fn comment_contains_code(line: &str) -> bool {
+pub fn comment_contains_code(line: &str, comment_tags: &[String]) -> bool {
     let line = if let Some(line) = line.trim().strip_prefix('#') {
         line.trim()
     } else {
@@ -47,6 +47,12 @@ pub fn comment_contains_code(line: &str) -> bool {
         return false;
     }
 
+    if let Some(first) = line.split(&[' ', ':']).next() {
+        if comment_tags.iter().any(|tag| tag == first) {
+            return false;
+        }
+    }
+
     if CODING_COMMENT_REGEX.is_match(line) {
         return false;
     }
@@ -97,142 +103,166 @@ mod tests {
 
     #[test]
     fn comment_contains_code_basic() {
-        assert!(comment_contains_code("# x = 1"));
-        assert!(comment_contains_code("#from foo import eradicate"));
-        assert!(comment_contains_code("#import eradicate"));
-        assert!(comment_contains_code(r#"#"key": value,"#));
-        assert!(comment_contains_code(r#"#"key": "value","#));
-        assert!(comment_contains_code(r#"#"key": 1 + 1,"#));
-        assert!(comment_contains_code("#'key': 1 + 1,"));
-        assert!(comment_contains_code(r#"#"key": {"#));
-        assert!(comment_contains_code("#}"));
-        assert!(comment_contains_code("#} )]"));
-
-        assert!(!comment_contains_code("#"));
-        assert!(!comment_contains_code("# This is a (real) comment."));
-        assert!(!comment_contains_code("# 123"));
-        assert!(!comment_contains_code("# 123.1"));
-        assert!(!comment_contains_code("# 1, 2, 3"));
-        assert!(!comment_contains_code("x = 1  # x = 1"));
+        assert!(comment_contains_code("# x = 1", &[]));
+        assert!(comment_contains_code("#from foo import eradicate", &[]));
+        assert!(comment_contains_code("#import eradicate", &[]));
+        assert!(comment_contains_code(r#"#"key": value,"#, &[]));
+        assert!(comment_contains_code(r#"#"key": "value","#, &[]));
+        assert!(comment_contains_code(r#"#"key": 1 + 1,"#, &[]));
+        assert!(comment_contains_code("#'key': 1 + 1,", &[]));
+        assert!(comment_contains_code(r#"#"key": {"#, &[]));
+        assert!(comment_contains_code("#}", &[]));
+        assert!(comment_contains_code("#} )]", &[]));
+
+        assert!(!comment_contains_code("#", &[]));
+        assert!(!comment_contains_code("# This is a (real) comment.", &[]));
+        assert!(!comment_contains_code("# 123", &[]));
+        assert!(!comment_contains_code("# 123.1", &[]));
+        assert!(!comment_contains_code("# 1, 2, 3", &[]));
+        assert!(!comment_contains_code("x = 1  # x = 1", &[]));
+        assert!(!comment_contains_code(
+            "# pylint: disable=redefined-outer-name",
+            &[]
+        ),);
         assert!(!comment_contains_code(
-            "# pylint: disable=redefined-outer-name"
+            "# Issue #999: This is not code",
+            &[]
         ));
-        assert!(!comment_contains_code("# Issue #999: This is not code"));
 
         // TODO(charlie): This should be `true` under aggressive mode.
-        assert!(!comment_contains_code("#},"));
+        assert!(!comment_contains_code("#},", &[]));
     }
 
     #[test]
     fn comment_contains_code_with_print() {
-        assert!(comment_contains_code("#print"));
-        assert!(comment_contains_code("#print(1)"));
-        assert!(comment_contains_code("#print 1"));
+        assert!(comment_contains_code("#print", &[]));
+        assert!(comment_contains_code("#print(1)", &[]));
+        assert!(comment_contains_code("#print 1", &[]));
 
-        assert!(!comment_contains_code("#to print"));
+        assert!(!comment_contains_code("#to print", &[]));
     }
 
     #[test]
     fn comment_contains_code_with_return() {
-        assert!(comment_contains_code("#return x"));
+        assert!(comment_contains_code("#return x", &[]));
 
-        assert!(!comment_contains_code("#to print"));
+        assert!(!comment_contains_code("#to print", &[]));
     }
 
     #[test]
     fn comment_contains_code_with_multiline() {
-        assert!(comment_contains_code("#else:"));
-        assert!(comment_contains_code("#  else  :  "));
-        assert!(comment_contains_code(r#"# "foo %d" % \\"#));
-        assert!(comment_contains_code("#elif True:"));
-        assert!(comment_contains_code("#x = foo("));
-        assert!(comment_contains_code("#except Exception:"));
-
-        assert!(!comment_contains_code("# this is = to that :("));
-        assert!(!comment_contains_code("#else"));
-        assert!(!comment_contains_code("#or else:"));
-        assert!(!comment_contains_code("#else True:"));
+        assert!(comment_contains_code("#else:", &[]));
+        assert!(comment_contains_code("#  else  :  ", &[]));
+        assert!(comment_contains_code(r#"# "foo %d" % \\"#, &[]));
+        assert!(comment_contains_code("#elif True:", &[]));
+        assert!(comment_contains_code("#x = foo(", &[]));
+        assert!(comment_contains_code("#except Exception:", &[]));
+
+        assert!(!comment_contains_code("# this is = to that :(", &[]));
+        assert!(!comment_contains_code("#else", &[]));
+        assert!(!comment_contains_code("#or else:", &[]));
+        assert!(!comment_contains_code("#else True:", &[]));
 
         // Unpacking assignments
         assert!(comment_contains_code(
-            "# user_content_type, _ = TimelineEvent.objects.using(db_alias).get_or_create("
-        ));
+            "# user_content_type, _ = TimelineEvent.objects.using(db_alias).get_or_create(",
+            &[]
+        ),);
         assert!(comment_contains_code(
-            "# (user_content_type, _) = TimelineEvent.objects.using(db_alias).get_or_create("
-        ));
+            "# (user_content_type, _) = TimelineEvent.objects.using(db_alias).get_or_create(",
+            &[]
+        ),);
         assert!(comment_contains_code(
-            "# ( user_content_type , _ )= TimelineEvent.objects.using(db_alias).get_or_create("
+            "# ( user_content_type , _ )= TimelineEvent.objects.using(db_alias).get_or_create(",
+            &[]
         ));
         assert!(comment_contains_code(
-            "#     app_label=\"core\", model=\"user\""
+            "#     app_label=\"core\", model=\"user\"",
+            &[]
         ));
-        assert!(comment_contains_code("# )"));
+        assert!(comment_contains_code("# )", &[]));
 
         // TODO(charlie): This should be `true` under aggressive mode.
-        assert!(!comment_contains_code("#def foo():"));
+        assert!(!comment_contains_code("#def foo():", &[]));
     }
 
     #[test]
     fn comment_contains_code_with_sentences() {
-        assert!(!comment_contains_code("#code is good"));
+        assert!(!comment_contains_code("#code is good", &[]));
     }
 
     #[test]
     fn comment_contains_code_with_encoding() {
-        assert!(comment_contains_code("# codings=utf-8"));
+        assert!(comment_contains_code("# codings=utf-8", &[]));
 
-        assert!(!comment_contains_code("# coding=utf-8"));
-        assert!(!comment_contains_code("#coding= utf-8"));
-        assert!(!comment_contains_code("# coding: utf-8"));
-        assert!(!comment_contains_code("# encoding: utf8"));
+        assert!(!comment_contains_code("# coding=utf-8", &[]));
+        assert!(!comment_contains_code("#coding= utf-8", &[]));
+        assert!(!comment_contains_code("# coding: utf-8", &[]));
+        assert!(!comment_contains_code("# encoding: utf8", &[]));
     }
 
     #[test]
     fn comment_contains_code_with_default_allowlist() {
-        assert!(!comment_contains_code("# pylint: disable=A0123"));
-        assert!(!comment_contains_code("# pylint:disable=A0123"));
-        assert!(!comment_contains_code("# pylint: disable = A0123"));
-        assert!(!comment_contains_code("# pylint:disable = A0123"));
-        assert!(!comment_contains_code("# pyright: reportErrorName=true"));
-        assert!(!comment_contains_code("# noqa"));
-        assert!(!comment_contains_code("# NOQA"));
-        assert!(!comment_contains_code("# noqa: A123"));
-        assert!(!comment_contains_code("# noqa:A123"));
-        assert!(!comment_contains_code("# nosec"));
-        assert!(!comment_contains_code("# fmt: on"));
-        assert!(!comment_contains_code("# fmt: off"));
-        assert!(!comment_contains_code("# fmt:on"));
-        assert!(!comment_contains_code("# fmt:off"));
-        assert!(!comment_contains_code("# isort: on"));
-        assert!(!comment_contains_code("# isort:on"));
-        assert!(!comment_contains_code("# isort: off"));
-        assert!(!comment_contains_code("# isort:off"));
-        assert!(!comment_contains_code("# isort: skip"));
-        assert!(!comment_contains_code("# isort:skip"));
-        assert!(!comment_contains_code("# isort: skip_file"));
-        assert!(!comment_contains_code("# isort:skip_file"));
-        assert!(!comment_contains_code("# isort: split"));
-        assert!(!comment_contains_code("# isort:split"));
-        assert!(!comment_contains_code("# isort: dont-add-imports"));
-        assert!(!comment_contains_code("# isort:dont-add-imports"));
+        assert!(!comment_contains_code("# pylint: disable=A0123", &[]));
+        assert!(!comment_contains_code("# pylint:disable=A0123", &[]));
+        assert!(!comment_contains_code("# pylint: disable = A0123", &[]));
+        assert!(!comment_contains_code("# pylint:disable = A0123", &[]));
+        assert!(!comment_contains_code(
+            "# pyright: reportErrorName=true",
+            &[]
+        ));
+        assert!(!comment_contains_code("# noqa", &[]));
+        assert!(!comment_contains_code("# NOQA", &[]));
+        assert!(!comment_contains_code("# noqa: A123", &[]));
+        assert!(!comment_contains_code("# noqa:A123", &[]));
+        assert!(!comment_contains_code("# nosec", &[]));
+        assert!(!comment_contains_code("# fmt: on", &[]));
+        assert!(!comment_contains_code("# fmt: off", &[]));
+        assert!(!comment_contains_code("# fmt:on", &[]));
+        assert!(!comment_contains_code("# fmt:off", &[]));
+        assert!(!comment_contains_code("# isort: on", &[]));
+        assert!(!comment_contains_code("# isort:on", &[]));
+        assert!(!comment_contains_code("# isort: off", &[]));
+        assert!(!comment_contains_code("# isort:off", &[]));
+        assert!(!comment_contains_code("# isort: skip", &[]));
+        assert!(!comment_contains_code("# isort:skip", &[]));
+        assert!(!comment_contains_code("# isort: skip_file", &[]));
+        assert!(!comment_contains_code("# isort:skip_file", &[]));
+        assert!(!comment_contains_code("# isort: split", &[]));
+        assert!(!comment_contains_code("# isort:split", &[]));
+        assert!(!comment_contains_code("# isort: dont-add-imports", &[]));
+        assert!(!comment_contains_code("# isort:dont-add-imports", &[]));
+        assert!(!comment_contains_code(
+            "# isort: dont-add-imports: [\"import os\"]",
+            &[]
+        ));
+        assert!(!comment_contains_code(
+            "# isort:dont-add-imports: [\"import os\"]",
+            &[]
+        ));
+        assert!(!comment_contains_code(
+            "# isort: dont-add-imports:[\"import os\"]",
+            &[]
+        ));
         assert!(!comment_contains_code(
-            "# isort: dont-add-imports: [\"import os\"]"
+            "# isort:dont-add-imports:[\"import os\"]",
+            &[]
         ));
+        assert!(!comment_contains_code("# type: ignore", &[]));
+        assert!(!comment_contains_code("# type:ignore", &[]));
+        assert!(!comment_contains_code("# type: ignore[import]", &[]));
+        assert!(!comment_contains_code("# type:ignore[import]", &[]));
         assert!(!comment_contains_code(
-            "# isort:dont-add-imports: [\"import os\"]"
+            "# TODO: Do that",
+            &["TODO".to_string()]
         ));
         assert!(!comment_contains_code(
-            "# isort: dont-add-imports:[\"import os\"]"
+            "# FIXME: Fix that",
+            &["FIXME".to_string()]
         ));
         assert!(!comment_contains_code(
-            "# isort:dont-add-imports:[\"import os\"]"
+            "# XXX: What ever",
+            &["XXX".to_string()]
         ));
-        assert!(!comment_contains_code("# type: ignore"));
-        assert!(!comment_contains_code("# type:ignore"));
-        assert!(!comment_contains_code("# type: ignore[import]"));
-        assert!(!comment_contains_code("# type:ignore[import]"));
-        assert!(!comment_contains_code("# TODO: Do that"));
-        assert!(!comment_contains_code("# FIXME: Fix that"));
-        assert!(!comment_contains_code("# XXX: What ever"));
     }
 }
diff --git a/src/lib_wasm.rs b/src/lib_wasm.rs
index 6a949dbbab3292..708bb50375104d 100644
--- a/src/lib_wasm.rs
+++ b/src/lib_wasm.rs
@@ -112,6 +112,7 @@ pub fn defaultSettings() -> Result<JsValue, JsValue> {
         show_source: None,
         src: None,
         unfixable: None,
+        comment_tags: None,
         update_check: None,
         // Use default options for all plugins.
         flake8_annotations: Some(flake8_annotations::settings::Settings::default().into()),
diff --git a/src/pycodestyle/checks.rs b/src/pycodestyle/checks.rs
index c4f5f893367be2..d4df80b281bb4d 100644
--- a/src/pycodestyle/checks.rs
+++ b/src/pycodestyle/checks.rs
@@ -8,34 +8,41 @@ use crate::ast::helpers::except_range;
 use crate::ast::types::Range;
 use crate::autofix::Fix;
 use crate::registry::{Check, CheckKind};
+use crate::settings::Settings;
 use crate::source_code_locator::SourceCodeLocator;
 
 static URL_REGEX: Lazy<Regex> = Lazy::new(|| Regex::new(r"^https?://\S+$").unwrap());
 
 /// E501
-pub fn line_too_long(lineno: usize, line: &str, max_line_length: usize) -> Option<Check> {
+pub fn line_too_long(lineno: usize, line: &str, settings: &Settings) -> Option<Check> {
     let line_length = line.chars().count();
 
-    if line_length <= max_line_length {
+    if line_length <= settings.line_length {
         return None;
     }
 
     let mut chunks = line.split_whitespace();
-    let (Some(first), Some(_)) = (chunks.next(), chunks.next()) else {
+    let (Some(first), Some(second)) = (chunks.next(), chunks.next()) else {
         // Single word / no printable chars - no way to make the line shorter
         return None;
     };
 
+    let second = second.trim_end_matches(':');
+
     // Do not enforce the line length for commented lines that end with a URL
     // or contain only a single word.
-    if first == "#" && chunks.last().map_or(true, |c| URL_REGEX.is_match(c)) {
+    if first == "#"
+        && ((settings.pycodestyle.allow_overlong_lines_for_comment_tags
+            && settings.comment_tags.iter().any(|tag| tag == second))
+            || chunks.last().map_or(true, |c| URL_REGEX.is_match(c)))
+    {
         return None;
     }
 
     Some(Check::new(
-        CheckKind::LineTooLong(line_length, max_line_length),
+        CheckKind::LineTooLong(line_length, settings.line_length),
         Range::new(
-            Location::new(lineno + 1, max_line_length),
+            Location::new(lineno + 1, settings.line_length),
             Location::new(lineno + 1, line_length),
         ),
     ))
diff --git a/src/pycodestyle/mod.rs b/src/pycodestyle/mod.rs
index 8027c14f3950e0..dbb2f59f339d2e 100644
--- a/src/pycodestyle/mod.rs
+++ b/src/pycodestyle/mod.rs
@@ -1,5 +1,6 @@
 pub mod checks;
 pub mod plugins;
+pub mod settings;
 
 #[cfg(test)]
 mod tests {
@@ -9,6 +10,7 @@ mod tests {
     use anyhow::Result;
     use test_case::test_case;
 
+    use super::settings::Settings;
     use crate::linter::test_path;
     use crate::registry::CheckCode;
     use crate::settings;
@@ -56,4 +58,20 @@ mod tests {
         insta::assert_yaml_snapshot!(checks);
         Ok(())
     }
+
+    #[test_case(false)]
+    #[test_case(true)]
+    fn e501_comment_tags(allow_overlong_lines_for_comment_tags: bool) -> Result<()> {
+        let checks = test_path(
+            Path::new("./resources/test/fixtures/pycodestyle/E501_1.py"),
+            &settings::Settings {
+                pycodestyle: Settings {
+                    allow_overlong_lines_for_comment_tags,
+                },
+                ..settings::Settings::for_rule(CheckCode::E501)
+            },
+        )?;
+        insta::assert_yaml_snapshot!(checks);
+        Ok(())
+    }
 }
diff --git a/src/pycodestyle/settings.rs b/src/pycodestyle/settings.rs
new file mode 100644
index 00000000000000..66d4071742527d
--- /dev/null
+++ b/src/pycodestyle/settings.rs
@@ -0,0 +1,47 @@
+//! Settings for the `pycodestyle` plugin.
+
+use ruff_macros::ConfigurationOptions;
+use schemars::JsonSchema;
+use serde::{Deserialize, Serialize};
+
+#[derive(
+    Debug, PartialEq, Eq, Serialize, Deserialize, Default, ConfigurationOptions, JsonSchema,
+)]
+#[serde(deny_unknown_fields, rename_all = "kebab-case", rename = "Pycodestyle")]
+pub struct Options {
+    #[option(
+        default = "false",
+        value_type = "bool",
+        example = r#"
+            allow-overlong-lines-for-comment-tags = true
+        "#
+    )]
+    /// Whether or not E501 (LineTooLong) should be triggered for comments
+    /// starting with one of the `comment-tags`.
+    pub allow_overlong_lines_for_comment_tags: Option<bool>,
+}
+
+#[derive(Debug, Default, Hash)]
+pub struct Settings {
+    pub allow_overlong_lines_for_comment_tags: bool,
+}
+
+impl From<Options> for Settings {
+    fn from(options: Options) -> Self {
+        Self {
+            allow_overlong_lines_for_comment_tags: options
+                .allow_overlong_lines_for_comment_tags
+                .unwrap_or_default(),
+        }
+    }
+}
+
+impl From<Settings> for Options {
+    fn from(settings: Settings) -> Self {
+        Self {
+            allow_overlong_lines_for_comment_tags: Some(
+                settings.allow_overlong_lines_for_comment_tags,
+            ),
+        }
+    }
+}
diff --git a/src/pycodestyle/snapshots/ruff__pycodestyle__tests__e501_comment_tags-2.snap b/src/pycodestyle/snapshots/ruff__pycodestyle__tests__e501_comment_tags-2.snap
new file mode 100644
index 00000000000000..803588cfbe0fc0
--- /dev/null
+++ b/src/pycodestyle/snapshots/ruff__pycodestyle__tests__e501_comment_tags-2.snap
@@ -0,0 +1,6 @@
+---
+source: src/pycodestyle/mod.rs
+expression: checks
+---
+[]
+
diff --git a/src/pycodestyle/snapshots/ruff__pycodestyle__tests__e501_comment_tags.snap b/src/pycodestyle/snapshots/ruff__pycodestyle__tests__e501_comment_tags.snap
new file mode 100644
index 00000000000000..d39c77667c2736
--- /dev/null
+++ b/src/pycodestyle/snapshots/ruff__pycodestyle__tests__e501_comment_tags.snap
@@ -0,0 +1,77 @@
+---
+source: src/pycodestyle/mod.rs
+expression: checks
+---
+- kind:
+    LineTooLong:
+      - 152
+      - 88
+  location:
+    row: 1
+    column: 88
+  end_location:
+    row: 1
+    column: 152
+  fix: ~
+  parent: ~
+- kind:
+    LineTooLong:
+      - 151
+      - 88
+  location:
+    row: 2
+    column: 88
+  end_location:
+    row: 2
+    column: 151
+  fix: ~
+  parent: ~
+- kind:
+    LineTooLong:
+      - 158
+      - 88
+  location:
+    row: 3
+    column: 88
+  end_location:
+    row: 3
+    column: 158
+  fix: ~
+  parent: ~
+- kind:
+    LineTooLong:
+      - 153
+      - 88
+  location:
+    row: 4
+    column: 88
+  end_location:
+    row: 4
+    column: 153
+  fix: ~
+  parent: ~
+- kind:
+    LineTooLong:
+      - 152
+      - 88
+  location:
+    row: 5
+    column: 88
+  end_location:
+    row: 5
+    column: 152
+  fix: ~
+  parent: ~
+- kind:
+    LineTooLong:
+      - 159
+      - 88
+  location:
+    row: 6
+    column: 88
+  end_location:
+    row: 6
+    column: 159
+  fix: ~
+  parent: ~
+
diff --git a/src/settings/configuration.rs b/src/settings/configuration.rs
index 370d813113cf9e..3a49e1a786ee08 100644
--- a/src/settings/configuration.rs
+++ b/src/settings/configuration.rs
@@ -22,7 +22,7 @@ use crate::settings::types::{
 use crate::{
     flake8_annotations, flake8_bugbear, flake8_errmsg, flake8_import_conventions,
     flake8_pytest_style, flake8_quotes, flake8_tidy_imports, flake8_unused_arguments, fs, isort,
-    mccabe, pep8_naming, pydocstyle, pyupgrade,
+    mccabe, pep8_naming, pycodestyle, pydocstyle, pyupgrade,
 };
 
 #[derive(Debug, Default)]
@@ -53,6 +53,7 @@ pub struct Configuration {
     pub target_version: Option<PythonVersion>,
     pub unfixable: Option<Vec<CheckCodePrefix>>,
     pub update_check: Option<bool>,
+    pub comment_tags: Option<Vec<String>>,
     // Plugins
     pub flake8_annotations: Option<flake8_annotations::settings::Options>,
     pub flake8_bugbear: Option<flake8_bugbear::settings::Options>,
@@ -65,6 +66,7 @@ pub struct Configuration {
     pub isort: Option<isort::settings::Options>,
     pub mccabe: Option<mccabe::settings::Options>,
     pub pep8_naming: Option<pep8_naming::settings::Options>,
+    pub pycodestyle: Option<pycodestyle::settings::Options>,
     pub pydocstyle: Option<pydocstyle::settings::Options>,
     pub pyupgrade: Option<pyupgrade::settings::Options>,
 }
@@ -149,6 +151,7 @@ impl Configuration {
                 .transpose()?,
             target_version: options.target_version,
             unfixable: options.unfixable,
+            comment_tags: options.comment_tags,
             update_check: options.update_check,
             // Plugins
             flake8_annotations: options.flake8_annotations,
@@ -162,6 +165,7 @@ impl Configuration {
             isort: options.isort,
             mccabe: options.mccabe,
             pep8_naming: options.pep8_naming,
+            pycodestyle: options.pycodestyle,
             pydocstyle: options.pydocstyle,
             pyupgrade: options.pyupgrade,
         })
@@ -209,6 +213,7 @@ impl Configuration {
             src: self.src.or(config.src),
             target_version: self.target_version.or(config.target_version),
             unfixable: self.unfixable.or(config.unfixable),
+            comment_tags: self.comment_tags.or(config.comment_tags),
             update_check: self.update_check.or(config.update_check),
             // Plugins
             flake8_annotations: self.flake8_annotations.or(config.flake8_annotations),
@@ -226,6 +231,7 @@ impl Configuration {
             isort: self.isort.or(config.isort),
             mccabe: self.mccabe.or(config.mccabe),
             pep8_naming: self.pep8_naming.or(config.pep8_naming),
+            pycodestyle: self.pycodestyle.or(config.pycodestyle),
             pydocstyle: self.pydocstyle.or(config.pydocstyle),
             pyupgrade: self.pyupgrade.or(config.pyupgrade),
         }
diff --git a/src/settings/mod.rs b/src/settings/mod.rs
index 612059daa23fa5..17989a56553528 100644
--- a/src/settings/mod.rs
+++ b/src/settings/mod.rs
@@ -24,7 +24,7 @@ use crate::settings::types::{
 use crate::{
     flake8_annotations, flake8_bugbear, flake8_errmsg, flake8_import_conventions,
     flake8_pytest_style, flake8_quotes, flake8_tidy_imports, flake8_unused_arguments, isort,
-    mccabe, one_time_warning, pep8_naming, pydocstyle, pyupgrade,
+    mccabe, one_time_warning, pep8_naming, pycodestyle, pydocstyle, pyupgrade,
 };
 
 pub mod configuration;
@@ -58,6 +58,7 @@ pub struct Settings {
     pub show_source: bool,
     pub src: Vec<PathBuf>,
     pub target_version: PythonVersion,
+    pub comment_tags: Vec<String>,
     pub update_check: bool,
     // Plugins
     pub flake8_annotations: flake8_annotations::settings::Settings,
@@ -71,6 +72,7 @@ pub struct Settings {
     pub isort: isort::settings::Settings,
     pub mccabe: mccabe::settings::Settings,
     pub pep8_naming: pep8_naming::settings::Settings,
+    pub pycodestyle: pycodestyle::settings::Settings,
     pub pydocstyle: pydocstyle::settings::Settings,
     pub pyupgrade: pyupgrade::settings::Settings,
 }
@@ -162,6 +164,9 @@ impl Settings {
                 .src
                 .unwrap_or_else(|| vec![project_root.to_path_buf()]),
             target_version: config.target_version.unwrap_or_default(),
+            comment_tags: config.comment_tags.unwrap_or_else(|| {
+                vec!["TODO".to_string(), "FIXME".to_string(), "XXX".to_string()]
+            }),
             update_check: config.update_check.unwrap_or(true),
             // Plugins
             flake8_annotations: config
@@ -208,6 +213,10 @@ impl Settings {
                 .pep8_naming
                 .map(std::convert::Into::into)
                 .unwrap_or_default(),
+            pycodestyle: config
+                .pycodestyle
+                .map(std::convert::Into::into)
+                .unwrap_or_default(),
             pydocstyle: config
                 .pydocstyle
                 .map(std::convert::Into::into)
@@ -241,6 +250,7 @@ impl Settings {
             show_source: false,
             src: vec![path_dedot::CWD.clone()],
             target_version: PythonVersion::Py310,
+            comment_tags: vec!["TODO".to_string(), "FIXME".to_string()],
             update_check: false,
             flake8_annotations: flake8_annotations::settings::Settings::default(),
             flake8_bugbear: flake8_bugbear::settings::Settings::default(),
@@ -253,6 +263,7 @@ impl Settings {
             isort: isort::settings::Settings::default(),
             mccabe: mccabe::settings::Settings::default(),
             pep8_naming: pep8_naming::settings::Settings::default(),
+            pycodestyle: pycodestyle::settings::Settings::default(),
             pydocstyle: pydocstyle::settings::Settings::default(),
             pyupgrade: pyupgrade::settings::Settings::default(),
         }
@@ -280,6 +291,7 @@ impl Settings {
             show_source: false,
             src: vec![path_dedot::CWD.clone()],
             target_version: PythonVersion::Py310,
+            comment_tags: vec!["TODO".to_string()],
             update_check: false,
             flake8_annotations: flake8_annotations::settings::Settings::default(),
             flake8_bugbear: flake8_bugbear::settings::Settings::default(),
@@ -292,6 +304,7 @@ impl Settings {
             isort: isort::settings::Settings::default(),
             mccabe: mccabe::settings::Settings::default(),
             pep8_naming: pep8_naming::settings::Settings::default(),
+            pycodestyle: pycodestyle::settings::Settings::default(),
             pydocstyle: pydocstyle::settings::Settings::default(),
             pyupgrade: pyupgrade::settings::Settings::default(),
         }
diff --git a/src/settings/options.rs b/src/settings/options.rs
index 8d23c6e0286446..46f5d39873e5b6 100644
--- a/src/settings/options.rs
+++ b/src/settings/options.rs
@@ -10,7 +10,7 @@ use crate::settings::types::{PythonVersion, SerializationFormat, Version};
 use crate::{
     flake8_annotations, flake8_bugbear, flake8_errmsg, flake8_import_conventions,
     flake8_pytest_style, flake8_quotes, flake8_tidy_imports, flake8_unused_arguments, isort,
-    mccabe, pep8_naming, pydocstyle, pyupgrade,
+    mccabe, pep8_naming, pycodestyle, pydocstyle, pyupgrade,
 };
 
 #[derive(
@@ -339,6 +339,14 @@ pub struct Options {
     )]
     /// A list of check code prefixes to consider un-autofix-able.
     pub unfixable: Option<Vec<CheckCodePrefix>>,
+    #[option(
+        default = r#"["TODO", "FIXME", "XXX"]"#,
+        value_type = "Vec<String>",
+        example = r#"comment-tags = ["TODO", "FIXME", "HACK"]"#
+    )]
+    /// A list of comment tags to recognize (e.g. TODO, FIXME, XXX).
+    /// Comments starting with these tags will be skipped by E501 and ERA001.
+    pub comment_tags: Option<Vec<String>>,
     #[option(
         default = "true",
         value_type = "bool",
@@ -381,6 +389,9 @@ pub struct Options {
     /// Options for the `pep8-naming` plugin.
     pub pep8_naming: Option<pep8_naming::settings::Options>,
     #[option_group]
+    /// Options for the `pycodestyle` plugin.
+    pub pycodestyle: Option<pycodestyle::settings::Options>,
+    #[option_group]
     /// Options for the `pydocstyle` plugin.
     pub pydocstyle: Option<pydocstyle::settings::Options>,
     #[option_group]
diff --git a/src/settings/pyproject.rs b/src/settings/pyproject.rs
index 8c02c31248dc27..d1c03fa5923b6b 100644
--- a/src/settings/pyproject.rs
+++ b/src/settings/pyproject.rs
@@ -188,6 +188,7 @@ mod tests {
                     src: None,
                     target_version: None,
                     unfixable: None,
+                    comment_tags: None,
                     update_check: None,
                     flake8_annotations: None,
                     flake8_bugbear: None,
@@ -200,6 +201,7 @@ mod tests {
                     isort: None,
                     mccabe: None,
                     pep8_naming: None,
+                    pycodestyle: None,
                     pydocstyle: None,
                     pyupgrade: None,
                 })
@@ -241,6 +243,7 @@ line-length = 79
                     src: None,
                     target_version: None,
                     unfixable: None,
+                    comment_tags: None,
                     update_check: None,
                     cache_dir: None,
                     flake8_annotations: None,
@@ -254,6 +257,7 @@ line-length = 79
                     isort: None,
                     mccabe: None,
                     pep8_naming: None,
+                    pycodestyle: None,
                     pydocstyle: None,
                     pyupgrade: None,
                 })
@@ -296,6 +300,7 @@ exclude = ["foo.py"]
                     src: None,
                     target_version: None,
                     unfixable: None,
+                    comment_tags: None,
                     update_check: None,
                     flake8_annotations: None,
                     flake8_errmsg: None,
@@ -308,6 +313,7 @@ exclude = ["foo.py"]
                     isort: None,
                     mccabe: None,
                     pep8_naming: None,
+                    pycodestyle: None,
                     pydocstyle: None,
                     pyupgrade: None,
                 })
@@ -350,6 +356,7 @@ select = ["E501"]
                     src: None,
                     target_version: None,
                     unfixable: None,
+                    comment_tags: None,
                     update_check: None,
                     flake8_annotations: None,
                     flake8_bugbear: None,
@@ -362,6 +369,7 @@ select = ["E501"]
                     isort: None,
                     mccabe: None,
                     pep8_naming: None,
+                    pycodestyle: None,
                     pydocstyle: None,
                     pyupgrade: None,
                 })
@@ -405,6 +413,7 @@ ignore = ["E501"]
                     src: None,
                     target_version: None,
                     unfixable: None,
+                    comment_tags: None,
                     update_check: None,
                     flake8_annotations: None,
                     flake8_bugbear: None,
@@ -417,6 +426,7 @@ ignore = ["E501"]
                     isort: None,
                     mccabe: None,
                     pep8_naming: None,
+                    pycodestyle: None,
                     pydocstyle: None,
                     pyupgrade: None,
                 })
@@ -490,6 +500,7 @@ other-attribute = 1
                 format: None,
                 force_exclude: None,
                 unfixable: None,
+                comment_tags: None,
                 update_check: None,
                 cache_dir: None,
                 per_file_ignores: Some(FxHashMap::from_iter([(
@@ -592,6 +603,7 @@ other-attribute = 1
                     ]),
                     staticmethod_decorators: Some(vec!["staticmethod".to_string()]),
                 }),
+                pycodestyle: None,
                 pydocstyle: None,
                 pyupgrade: None,
             }