diff --git a/src/app.rs b/src/app.rs
index f5c7a11..ca05927 100644
--- a/src/app.rs
+++ b/src/app.rs
@@ -22,8 +22,14 @@ pub fn update(base_config: &Config, new_version: &Version) -> Result<()> {
         replace: "current_version = \\\"{{new_version}}\\\"".to_string(),
     });
     for f in files {
-        let search_text = Tera::one_off(&f.search, &ctx, true).unwrap();
-        let replace_text = Tera::one_off(&f.replace, &ctx, true).unwrap();
+        let search_text = Tera::one_off(&f.search, &ctx, true)
+            .unwrap()
+            .trim_start()
+            .to_string();
+        let replace_text = Tera::one_off(&f.replace, &ctx, true)
+            .unwrap()
+            .trim_start()
+            .to_string();
         let new_text = build_updates(read_to_string(&f.path).unwrap(), search_text, replace_text);
         let mut out = File::create(&f.path)?;
         let _ = out.write(new_text.as_bytes());
@@ -41,11 +47,22 @@ fn make_context(current_version: &Version, new_version: &Version) -> Context {
 }
 
 fn build_updates(input: String, seach_text: String, replace_text: String) -> String {
+    let lines = seach_text.split("\n").count();
+    println!("{}", lines);
+    let mut buf: Vec<String> = Vec::new();
     let mut output: Vec<String> = Vec::new();
     for line in input.split("\n") {
-        if line == seach_text {
+        if buf.len() == lines {
+            output.push(buf.pop().unwrap());
+        }
+        buf.push(line.to_string());
+        if buf.join("\n") == seach_text {
             output.push(replace_text.to_string());
-        } else {
+            buf.clear();
+        }
+    }
+    if buf.len() > 0 {
+        for line in buf {
             output.push(line.to_string());
         }
     }
diff --git a/tests/test_update.py b/tests/test_update.py
index 91b2e0f..ca8ae3b 100644
--- a/tests/test_update.py
+++ b/tests/test_update.py
@@ -72,3 +72,33 @@ def test_valid_conf__single_line(cmd, tmp_path: Path):  # noqa: D103
     proc = cmd("0.2.0")
     assert proc.returncode == 0
     assert data_txt.read_text() == "0.2.0"
+
+
+def test_valid_conf__multi_line(cmd, tmp_path: Path):  # noqa: D103
+    conf_text = textwrap.dedent(
+        '''\
+    current_version = "0.0.0"
+
+    [[files]]
+    path = "data.txt"
+    search = """
+    Target
+    ======
+    """
+    replace = """
+    Target
+    ======
+
+    v {{new_version}}
+    -----------------
+    """
+    '''
+    )
+    (tmp_path / ".age.toml").write_text(conf_text)
+    data_txt = tmp_path / "data.txt"
+    data_txt.write_text("Target\n======\n")
+
+    proc = cmd("0.2.0")
+    assert proc.returncode == 0
+    assert len(data_txt.read_text().split("\n")) == 6
+    assert "v 0.2.0" in data_txt.read_text()