diff --git a/src/configuration/builder.rs b/src/configuration/builder.rs
index 81b0275..3f15de3 100644
--- a/src/configuration/builder.rs
+++ b/src/configuration/builder.rs
@@ -79,6 +79,12 @@ impl ConfigurationBuilder {
     self.insert("unorderedListKind", value.to_string().into())
   }
 
+  /// The type of heading to use.
+  /// Default: `HeadingKind::Atx`
+  pub fn heading_kind(&mut self, value: HeadingKind) -> &mut Self {
+    self.insert("headingKind", value.to_string().into())
+  }
+
   /// The directive used to ignore a line.
   /// Default: `dprint-ignore`
   pub fn ignore_directive(&mut self, value: &str) -> &mut Self {
@@ -140,13 +146,14 @@ mod tests {
       .emphasis_kind(EmphasisKind::Asterisks)
       .strong_kind(StrongKind::Underscores)
       .unordered_list_kind(UnorderedListKind::Asterisks)
+      .heading_kind(HeadingKind::Atx)
       .ignore_directive("test")
       .ignore_file_directive("test")
       .ignore_start_directive("test")
       .ignore_end_directive("test");
 
     let inner_config = config.get_inner_config();
-    assert_eq!(inner_config.len(), 10);
+    assert_eq!(inner_config.len(), 11);
     let diagnostics = resolve_config(inner_config, &Default::default()).diagnostics;
     assert_eq!(diagnostics.len(), 0);
   }
diff --git a/src/configuration/resolve_config.rs b/src/configuration/resolve_config.rs
index 6d7fd79..336d5a6 100644
--- a/src/configuration/resolve_config.rs
+++ b/src/configuration/resolve_config.rs
@@ -60,6 +60,7 @@ pub fn resolve_config(
       UnorderedListKind::Dashes,
       &mut diagnostics,
     ),
+    heading_kind: get_value(&mut config, "headingKind", HeadingKind::Atx, &mut diagnostics),
     ignore_directive: get_value(
       &mut config,
       "ignoreDirective",
diff --git a/src/configuration/types.rs b/src/configuration/types.rs
index 13c0bcb..139b8f0 100644
--- a/src/configuration/types.rs
+++ b/src/configuration/types.rs
@@ -13,6 +13,7 @@ pub struct Configuration {
   pub emphasis_kind: EmphasisKind,
   pub strong_kind: StrongKind,
   pub unordered_list_kind: UnorderedListKind,
+  pub heading_kind: HeadingKind,
   pub ignore_directive: String,
   pub ignore_file_directive: String,
   pub ignore_start_directive: String,
@@ -91,3 +92,20 @@ impl UnorderedListKind {
 }
 
 generate_str_to_from![UnorderedListKind, [Dashes, "dashes"], [Asterisks, "asterisks"]];
+
+/// The style of heading to use for level 1 and level headings:
+/// [setext](https://spec.commonmark.org/0.31.2/#setext-headings) or
+/// [ATX](https://spec.commonmark.org/0.31.2/#atx-headings). Level 3 and
+/// higher headings always use ATX headings, since Markdown only supports
+/// setext headers for levels 1 and 2.
+#[derive(Clone, PartialEq, Copy, Serialize, Deserialize)]
+#[serde(rename_all = "camelCase")]
+pub enum HeadingKind {
+  /// Uses an underline of `=` or `-` beneath the heading text for level 1 and
+  /// 2 headings.
+  Setext,
+  /// Uses `#` or `##` before the heading text for level 1 and 2 headings.
+  Atx,
+}
+
+generate_str_to_from![HeadingKind, [Setext, "setext"], [Atx, "atx"]];
diff --git a/src/generation/generate.rs b/src/generation/generate.rs
index 227fe4b..d304948 100644
--- a/src/generation/generate.rs
+++ b/src/generation/generate.rs
@@ -276,8 +276,33 @@ fn gen_nodes(nodes: &[Node], context: &mut Context) -> PrintItems {
 fn gen_heading(heading: &Heading, context: &mut Context) -> PrintItems {
   let mut items = PrintItems::new();
 
-  items.push_string(format!("{} ", "#".repeat(heading.level as usize)));
-  items.extend(with_no_new_lines(gen_nodes(&heading.children, context)));
+  if heading.level < 3 && context.configuration.heading_kind == HeadingKind::Setext {
+    // setext headings only apply to level 1 and level 2.
+    //
+    // First, output the heading text.
+    let heading_children = gen_nodes(&heading.children, context);
+    items.extend(heading_children);
+    items.push_item(PrintItem::Signal(Signal::NewLine));
+
+    // Next, create an underline. To produce a visually appealing underline,
+    // split the heading text (which may contain more than one line) into
+    // lines, then determine the length of the longest line. Note that this
+    // length should be determined **after** formatting, since lines may be
+    // wrapped during the formatting process.
+    //
+    // Incorrect -- need some way to get the text of the heading after's its
+    // been formatted/line wrapped. How to insert some sort of post-processing
+    // node?
+    //let heading_text = heading_children.get_as_text();
+    // For now, use a constant width.
+    let heading_text = "x".repeat(context.configuration.line_width as usize);
+    // For now, use constant-width dummy text.
+    items.push_string((if heading.level == 1 { "=" } else { "-" }).repeat(heading_text.len()));
+  } else {
+    // atx headings apply to all levels.
+    items.push_string(format!("{} ", "#".repeat(heading.level as usize)));
+    items.extend(with_no_new_lines(gen_nodes(&heading.children, context)));
+  }
 
   items
 }
diff --git a/tests/specs/headers/Headers_All.txt b/tests/specs/headers/Headers_All.txt
index 1fb24b5..94a3f46 100644
--- a/tests/specs/headers/Headers_All.txt
+++ b/tests/specs/headers/Headers_All.txt
@@ -1,4 +1,4 @@
-~~ lineWidth: 40 ~~
+~~ lineWidth: 40, textWrap: always ~~
 !! should format the headers !!
 # H1
 
@@ -37,9 +37,14 @@ Second Header
 !! should keep a header on a single line even when it goes over the line width !!
 # Testing this out by going over the line width
 
+Verifying that text is wrapping in other places.
+
 [expect]
 # Testing this out by going over the line width
 
+Verifying that text is wrapping in other
+places.
+
 !! should remove consecutive spaces in the header text !!
 # Here   is      a           test
 
diff --git a/tests/specs/headers/Headers_All_Setext.txt b/tests/specs/headers/Headers_All_Setext.txt
new file mode 100644
index 0000000..bf2f182
--- /dev/null
+++ b/tests/specs/headers/Headers_All_Setext.txt
@@ -0,0 +1,45 @@
+~~ lineWidth: 40, headingKind: setext ~~
+!! should format the headers !!
+# H1
+
+## H2
+
+### H3
+
+#### H4
+
+First Header
+============
+
+Second Header
+-------------
+
+[expect]
+H1
+========================================
+
+H2
+----------------------------------------
+
+### H3
+
+#### H4
+
+First Header
+========================================
+
+Second Header
+----------------------------------------
+
+!! Headers are allowed to flow over multiple lines.
+This Header
+spans
+multiple lines
+========================================
+
+
+[expect]
+This Header
+spans
+multiple lines
+========================================