diff --git a/Cargo.lock b/Cargo.lock
index 9de445fd..ec101507 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -4745,6 +4745,7 @@ dependencies = [
  "serde",
  "serde_json",
  "serde_yaml",
+ "textwrap",
  "thiserror",
  "walkdir",
  "weaver_common",
diff --git a/crates/weaver_forge/Cargo.toml b/crates/weaver_forge/Cargo.toml
index 05cc34a9..105731cc 100644
--- a/crates/weaver_forge/Cargo.toml
+++ b/crates/weaver_forge/Cargo.toml
@@ -29,6 +29,7 @@ jaq-syn = "1.1.0"
 indexmap = "2.6.0"
 regex = "1.11.1"
 markdown = "=1.0.0-alpha.21"
+textwrap = "0.16.1"
 
 itertools.workspace = true
 thiserror.workspace = true
diff --git a/crates/weaver_forge/src/config.rs b/crates/weaver_forge/src/config.rs
index c14a1604..d94a7a79 100644
--- a/crates/weaver_forge/src/config.rs
+++ b/crates/weaver_forge/src/config.rs
@@ -322,6 +322,8 @@ pub struct CommentFormat {
     /// Flag to enforce trailing dots on the comment content.
     #[serde(default = "default_bool::<false>")]
     pub enforce_trailing_dots: bool,
+    /// The maximum number of characters in a line.
+    pub(crate) line_length: Option<usize>,
 }
 
 /// The type of indentation to use for the comment.
diff --git a/crates/weaver_forge/src/extensions/code.rs b/crates/weaver_forge/src/extensions/code.rs
index 8b6fdbe0..be39de41 100644
--- a/crates/weaver_forge/src/extensions/code.rs
+++ b/crates/weaver_forge/src/extensions/code.rs
@@ -9,6 +9,7 @@ use crate::formats::markdown::MarkdownRenderer;
 use minijinja::value::{Kwargs, ValueKind};
 use minijinja::{Environment, ErrorKind, Value};
 use std::collections::HashMap;
+use std::usize;
 
 /// Add code-oriented filters to the environment.
 ///
@@ -176,26 +177,43 @@ pub(crate) fn comment(
                 .map(|v: String| v)
                 .unwrap_or_else(|_| comment_format.footer.clone().unwrap_or("".to_owned()));
 
+            // Configure text-wrap algorithm to appropriately segment lines.
+            let subsequent_indent = format!("{indent}{prefix}");
+            // If there is a header, then we need to indent the first line.
+            let initial_indent = if header.is_empty() {
+                &prefix
+            } else {
+                &subsequent_indent
+            };
+            let wrap_options =
+                textwrap::Options::new(comment_format.line_length.unwrap_or(usize::MAX))
+                    .initial_indent(&initial_indent)
+                    .subsequent_indent(&subsequent_indent)
+                    .wrap_algorithm(textwrap::WrapAlgorithm::FirstFit)
+                    .break_words(false);
+            // Wrap the comment as configured.
+            comment = textwrap::fill(&comment, wrap_options);
+
+            // The textwrap will leave empty lines, which we want to fill with the prefix.
             let mut new_comment = String::new();
             for line in comment.lines() {
                 if !new_comment.is_empty() {
                     new_comment.push('\n');
                 }
-                if header.is_empty() && new_comment.is_empty() {
-                    // For the first line we don't add the indentation
-                    new_comment.push_str(&format!("{}{}", prefix, line));
+                if line.is_empty() && !new_comment.is_empty() {
+                    new_comment.push_str(&format!("{indent}{prefix}"));
                 } else {
-                    new_comment.push_str(&format!("{}{}{}", indent, prefix, line));
+                    new_comment.push_str(line);
                 }
             }
             comment = new_comment;
 
+            // Add header + footer to the comment.
             if !header.is_empty() {
                 comment = format!("{}\n{}", header, comment);
             }
-
             if !footer.is_empty() {
-                comment = format!("{}\n{}{}", comment, indent, footer);
+                comment = format!("{}\n{}{}", comment.trim_end(), indent, footer);
             }
 
             // Remove all trailing spaces from the comment
@@ -285,6 +303,7 @@ mod tests {
                         trim: true,
                         remove_trailing_dots: true,
                         enforce_trailing_dots: false,
+                        line_length: None,
                     },
                 )]
                 .into_iter()
@@ -462,6 +481,7 @@ it's RECOMMENDED to:
                         trim: true,
                         remove_trailing_dots: true,
                         enforce_trailing_dots: false,
+                        line_length: None,
                     },
                 )]
                 .into_iter()
@@ -523,6 +543,7 @@ it's RECOMMENDED to:
                         remove_trailing_dots: true,
                         enforce_trailing_dots: false,
                         indent_type: Default::default(),
+                        line_length: None,
                     },
                 )]
                 .into_iter()
@@ -589,6 +610,7 @@ it's RECOMMENDED to:
                         remove_trailing_dots: false,
                         enforce_trailing_dots: true,
                         indent_type: Default::default(),
+                        line_length: None,
                     },
                 )]
                 .into_iter()
diff --git a/crates/weaver_forge/src/formats/html.rs b/crates/weaver_forge/src/formats/html.rs
index cd6fed43..ce502388 100644
--- a/crates/weaver_forge/src/formats/html.rs
+++ b/crates/weaver_forge/src/formats/html.rs
@@ -351,6 +351,7 @@ mod tests {
                         trim: true,
                         remove_trailing_dots: true,
                         enforce_trailing_dots: false,
+                        line_length: None,
                     },
                 )]
                 .into_iter()
diff --git a/crates/weaver_forge/src/formats/markdown.rs b/crates/weaver_forge/src/formats/markdown.rs
index 3dea59f3..b7cf42fb 100644
--- a/crates/weaver_forge/src/formats/markdown.rs
+++ b/crates/weaver_forge/src/formats/markdown.rs
@@ -412,6 +412,7 @@ mod tests {
                         trim: true,
                         remove_trailing_dots: true,
                         enforce_trailing_dots: false,
+                        line_length: None,
                     },
                 )]
                 .into_iter()
@@ -517,6 +518,7 @@ it's RECOMMENDED to:
                         remove_trailing_dots: true,
                         indent_type: Default::default(),
                         enforce_trailing_dots: false,
+                        line_length: None,
                     },
                 )]
                 .into_iter()
@@ -557,6 +559,7 @@ The file \[extension\] extracted \[from] the `url.full`, excluding the leading d
                         remove_trailing_dots: true,
                         indent_type: Default::default(),
                         enforce_trailing_dots: false,
+                        line_length: None,
                     },
                 )]
                 .into_iter()