diff --git a/CHANGELOG.md b/CHANGELOG.md
index 77bf95241..2db870f8b 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -20,6 +20,8 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 - Ensure `@tailwindcss/vite` doesn't crash during HMR when scanned files or directories are deleted ([#20259](https://github.com/tailwindlabs/tailwindcss/pull/20259))
 - Ensure `text-[--spacing(…)]` generates `font-size` instead of `color` ([#20260](https://github.com/tailwindlabs/tailwindcss/pull/20260))
 - Prevent `@source` patterns from scanning unrelated sibling files and folders ([#20263](https://github.com/tailwindlabs/tailwindcss/pull/20263))
+- Extract class candidates adjacent to Template Toolkit delimiters like `%]…[%` in `.tt`, `.tt2`, and `.tx` files ([#20269](https://github.com/tailwindlabs/tailwindcss/pull/20269))
+- Extract class candidates from conditional Maud syntax like `p.text-black[condition]` ([#20269](https://github.com/tailwindlabs/tailwindcss/pull/20269))
 
 ## [4.3.1] - 2026-06-12
 
diff --git a/crates/oxide/src/extractor/mod.rs b/crates/oxide/src/extractor/mod.rs
index a37d6a0a4..a3d806a27 100644
--- a/crates/oxide/src/extractor/mod.rs
+++ b/crates/oxide/src/extractor/mod.rs
@@ -908,6 +908,18 @@ mod tests {
         );
     }
 
+    // https://github.com/tailwindlabs/tailwindcss/issues/20233
+    #[test]
+    fn test_template_toolkit_syntax() {
+        assert_extract_candidates_contains(
+            &pre_process_input(
+                r#"<div class="[% IF $is_open %]bg-white/40[% ELSE %]bg-white/10[% END %]"></div>"#,
+                "tx",
+            ),
+            vec!["bg-white/40", "bg-white/10"],
+        );
+    }
+
     // https://github.com/tailwindlabs/tailwindcss/issues/17050
     #[test]
     fn test_haml_syntax() {
diff --git a/crates/oxide/src/extractor/pre_processors/mod.rs b/crates/oxide/src/extractor/pre_processors/mod.rs
index 1876ec6aa..1a04af5c9 100644
--- a/crates/oxide/src/extractor/pre_processors/mod.rs
+++ b/crates/oxide/src/extractor/pre_processors/mod.rs
@@ -10,6 +10,7 @@ pub mod ruby;
 pub mod rust;
 pub mod slim;
 pub mod svelte;
+pub mod template_toolkit;
 pub mod twig;
 pub mod vue;
 
@@ -25,5 +26,6 @@ pub use ruby::*;
 pub use rust::*;
 pub use slim::*;
 pub use svelte::*;
+pub use template_toolkit::*;
 pub use twig::*;
 pub use vue::*;
diff --git a/crates/oxide/src/extractor/pre_processors/rust.rs b/crates/oxide/src/extractor/pre_processors/rust.rs
index 34c9e0c91..4fa53f793 100644
--- a/crates/oxide/src/extractor/pre_processors/rust.rs
+++ b/crates/oxide/src/extractor/pre_processors/rust.rs
@@ -104,6 +104,12 @@ impl Rust {
 
                 b'[' => {
                     bracket_stack.push(cursor.curr());
+
+                    // Handle `p.flex[condition]`. If there is a `-` before it, it will likely be an
+                    // arbitrary value e.g. `text-[red]`
+                    if !matches!(cursor.prev(), b'-') {
+                        result[cursor.pos] = b' ';
+                    }
                 }
 
                 b']' if !bracket_stack.is_empty() => {
@@ -213,4 +219,20 @@ mod tests {
         let input = r#"html! { \x.px-4.text-black {  } }"#;
         Rust::test(input, r#"html! { \x px-4 text-black {  } }"#);
     }
+
+    // https://github.com/tailwindlabs/tailwindcss/issues/20233
+    #[test]
+    fn test_maud_template_extraction_with_conditional_classes() {
+        let input = r#"
+            use maud::{html, Markup};
+
+            pub fn main() -> Markup {
+                html! {
+                    p.text-black[cuteness > 50] { "Squee!" }
+                }
+            }
+        "#;
+
+        Rust::test_extract_contains(input, vec!["text-black"]);
+    }
 }
diff --git a/crates/oxide/src/extractor/pre_processors/template_toolkit.rs b/crates/oxide/src/extractor/pre_processors/template_toolkit.rs
new file mode 100644
index 000000000..6456a2694
--- /dev/null
+++ b/crates/oxide/src/extractor/pre_processors/template_toolkit.rs
@@ -0,0 +1,52 @@
+use crate::cursor;
+use crate::extractor::pre_processors::pre_processor::PreProcessor;
+
+#[derive(Debug, Default)]
+pub struct TemplateToolkit;
+
+impl PreProcessor for TemplateToolkit {
+    fn process(&self, content: &[u8]) -> Vec<u8> {
+        let len = content.len();
+        let mut result = content.to_vec();
+        let mut cursor = cursor::Cursor::new(content);
+
+        while cursor.pos < len {
+            match (cursor.curr(), cursor.next()) {
+                (b'[', b'%') => result[cursor.pos] = b' ',
+                (b'%', b']') => result[cursor.pos + 1] = b' ',
+                _ => {}
+            }
+
+            cursor.advance();
+        }
+
+        result
+    }
+}
+
+#[cfg(test)]
+mod tests {
+    use super::TemplateToolkit;
+    use crate::extractor::pre_processors::pre_processor::PreProcessor;
+
+    #[test]
+    fn test_template_toolkit_pre_processor() {
+        for (input, expected) in [
+            (
+                "[% IF $is_open %]bg-white/40[% ELSE %]bg-white/10[% END %]",
+                " % IF $is_open % bg-white/40 % ELSE % bg-white/10 % END % ",
+            ),
+            ("[% WRAPPER %]flex[% END %]", " % WRAPPER % flex % END % "),
+        ] {
+            TemplateToolkit::test(input, expected);
+        }
+    }
+
+    #[test]
+    fn test_extraction_between_template_tags_works() {
+        TemplateToolkit::test_extract_contains(
+            r#"<div class="[% IF $is_open %]bg-white/40[% ELSE %]bg-white/10[% END %]"></div>"#,
+            vec!["bg-white/40", "bg-white/10"],
+        );
+    }
+}
diff --git a/crates/oxide/src/scanner/mod.rs b/crates/oxide/src/scanner/mod.rs
index d665b2f4d..02830555d 100644
--- a/crates/oxide/src/scanner/mod.rs
+++ b/crates/oxide/src/scanner/mod.rs
@@ -480,6 +480,7 @@ pub fn pre_process_input(content: Vec<u8>, extension: &str) -> Vec<u8> {
         "slim" | "slang" => Slim.process(&content),
         "svelte" => Svelte.process(&content),
         "rs" => Rust.process(&content),
+        "tt" | "tt2" | "tx" => TemplateToolkit.process(&content),
         "twig" => Twig.process(&content),
         "vue" => Vue.process(&content),
         _ => content,