diff --git a/crates/classification-macros/src/lib.rs b/crates/classification-macros/src/lib.rs
index 4e10fc5ad..7bee55595 100644
--- a/crates/classification-macros/src/lib.rs
+++ b/crates/classification-macros/src/lib.rs
@@ -107,6 +107,12 @@ pub fn classify_bytes_derive(input: TokenStream) -> TokenStream {
                 #enum_name::TABLE[byte as usize]
             }
         }
+
+        impl From<&u8> for #enum_name {
+            fn from(byte: &u8) -> Self {
+                #enum_name::TABLE[*byte as usize]
+            }
+        }
     };
 
     TokenStream::from(expanded)
diff --git a/crates/oxide/src/extractor/boundary.rs b/crates/oxide/src/extractor/boundary.rs
new file mode 100644
index 000000000..3d13d895c
--- /dev/null
+++ b/crates/oxide/src/extractor/boundary.rs
@@ -0,0 +1,104 @@
+use classification_macros::ClassifyBytes;
+
+use crate::extractor::Span;
+
+#[inline(always)]
+pub fn is_valid_before_boundary(c: &u8) -> bool {
+    matches!(c.into(), Class::Common | Class::Before)
+}
+
+#[inline(always)]
+pub fn is_valid_after_boundary(c: &u8) -> bool {
+    matches!(c.into(), Class::Common | Class::After)
+}
+
+#[inline(always)]
+pub fn has_valid_boundaries(span: &Span, input: &[u8]) -> bool {
+    let before = {
+        if span.start == 0 {
+            b'\0'
+        } else {
+            input[span.start - 1]
+        }
+    };
+
+    let after = {
+        if span.end >= input.len() - 1 {
+            b'\0'
+        } else {
+            input[span.end + 1]
+        }
+    };
+
+    // Ensure the span has valid boundary characters before and after
+    is_valid_before_boundary(&before) && is_valid_after_boundary(&after)
+}
+
+#[derive(Debug, Clone, Copy, ClassifyBytes)]
+enum Class {
+    // Whitespace, e.g.:
+    //
+    // ```
+    // <div class="flex flex-col items-center"></div>
+    //                 ^        ^
+    // ```
+    #[bytes(b'\t', b'\n', b'\x0C', b'\r', b' ')]
+    // Quotes, e.g.:
+    //
+    // ```
+    // <div class="flex">
+    //            ^    ^
+    // ```
+    #[bytes(b'"', b'\'', b'`')]
+    // End of the input, e.g.:
+    //
+    // ```
+    // flex
+    //     ^
+    // ```
+    #[bytes(b'\0')]
+    Common,
+
+    // Angular like attributes, e.g.:
+    //
+    // ````
+    // [class.foo]
+    //       ^
+    // ```
+    #[bytes(b'.')]
+    // Twig-like templating languages, e.g.:
+    //
+    // ```
+    // <div class="{% if true %}flex{% else %}block{% endif %}">
+    //                         ^
+    // ```
+    #[bytes(b'}')]
+    Before,
+
+    // Clojure and Angular like languages, e.g.:
+    // ```
+    // [:div.p-2]
+    //          ^
+    // [class.foo]
+    //           ^
+    // ```
+    #[bytes(b']')]
+    // Twig like templating languages, e.g.:
+    //
+    // ```
+    // <div class="{% if true %}flex{% else %}block{% endif %}">
+    //                              ^
+    // ```
+    #[bytes(b'{')]
+    // Svelte like attributes, e.g.:
+    //
+    // ```
+    // <div class:flex="bool"></div>
+    //                ^
+    // ```
+    #[bytes(b'=')]
+    After,
+
+    #[fallback]
+    Other,
+}
diff --git a/crates/oxide/src/extractor/candidate_machine.rs b/crates/oxide/src/extractor/candidate_machine.rs
index e998c17d5..1d92ea153 100644
--- a/crates/oxide/src/extractor/candidate_machine.rs
+++ b/crates/oxide/src/extractor/candidate_machine.rs
@@ -1,4 +1,5 @@
 use crate::cursor;
+use crate::extractor::boundary::{has_valid_boundaries, is_valid_before_boundary};
 use crate::extractor::machine::{Machine, MachineState};
 use crate::extractor::utility_machine::UtilityMachine;
 use crate::extractor::variant_machine::VariantMachine;
@@ -176,56 +177,6 @@ impl CandidateMachine {
     }
 }
 
-/// A candidate must be preceded or followed by any of these characters
-/// E.g.: `<div class="flex">`
-///                   ^ Valid for `flex`
-///        ^ Invalid for `div`
-#[inline(always)]
-fn is_valid_common_boundary(c: &u8) -> bool {
-    matches!(
-        c,
-        b'\t' | b'\n' | b'\x0C' | b'\r' | b' ' | b'"' | b'\'' | b'`' | b'\0'
-    )
-}
-
-/// A candidate must be preceded by any of these characters.
-#[inline(always)]
-fn is_valid_before_boundary(c: &u8) -> bool {
-    is_valid_common_boundary(c) || matches!(c, b'.' | b'}')
-}
-
-/// A candidate must be followed by any of these characters.
-///
-/// E.g.: `[class.foo]`             Angular
-/// E.g.: `<div class:flex="bool">` Svelte
-///                       ^
-#[inline(always)]
-pub fn is_valid_after_boundary(c: &u8) -> bool {
-    is_valid_common_boundary(c) || matches!(c, b'}' | b']' | b'=' | b'{')
-}
-
-#[inline(always)]
-fn has_valid_boundaries(span: &Span, input: &[u8]) -> bool {
-    let before = {
-        if span.start == 0 {
-            b'\0'
-        } else {
-            input[span.start - 1]
-        }
-    };
-
-    let after = {
-        if span.end >= input.len() - 1 {
-            b'\0'
-        } else {
-            input[span.end + 1]
-        }
-    };
-
-    // Ensure the span has valid boundary characters before and after
-    is_valid_before_boundary(&before) && is_valid_after_boundary(&after)
-}
-
 #[cfg(test)]
 mod tests {
     use super::CandidateMachine;
diff --git a/crates/oxide/src/extractor/mod.rs b/crates/oxide/src/extractor/mod.rs
index a3e16c6ca..baf983831 100644
--- a/crates/oxide/src/extractor/mod.rs
+++ b/crates/oxide/src/extractor/mod.rs
@@ -8,6 +8,7 @@ use std::fmt;
 pub mod arbitrary_property_machine;
 pub mod arbitrary_value_machine;
 pub mod arbitrary_variable_machine;
+mod boundary;
 pub mod bracket_stack;
 pub mod candidate_machine;
 pub mod css_variable_machine;
diff --git a/crates/oxide/src/extractor/named_utility_machine.rs b/crates/oxide/src/extractor/named_utility_machine.rs
index a4d3b9de0..ab09f95bc 100644
--- a/crates/oxide/src/extractor/named_utility_machine.rs
+++ b/crates/oxide/src/extractor/named_utility_machine.rs
@@ -1,7 +1,7 @@
 use crate::cursor;
 use crate::extractor::arbitrary_value_machine::ArbitraryValueMachine;
 use crate::extractor::arbitrary_variable_machine::ArbitraryVariableMachine;
-use crate::extractor::candidate_machine::is_valid_after_boundary;
+use crate::extractor::boundary::is_valid_after_boundary;
 use crate::extractor::machine::{Machine, MachineState};
 use classification_macros::ClassifyBytes;
 
@@ -485,10 +485,7 @@ mod tests {
                     vec!["let", "classes", "true"],
                 ),
                 // Inside an object (no spaces, key)
-                (
-                    r#"let classes = {'{}':true};"#,
-                    vec!["let", "classes", "true"],
-                ),
+                (r#"let classes = {'{}':true};"#, vec!["let", "classes"]),
                 // Inside an object (value)
                 (
                     r#"let classes = { primary: '{}' };"#,
diff --git a/crates/oxide/src/extractor/pre_processors/ruby.rs b/crates/oxide/src/extractor/pre_processors/ruby.rs
index 09e775b2b..180101479 100644
--- a/crates/oxide/src/extractor/pre_processors/ruby.rs
+++ b/crates/oxide/src/extractor/pre_processors/ruby.rs
@@ -27,6 +27,7 @@ impl PreProcessor for Ruby {
             let boundary = match cursor.curr {
                 b'[' => b']',
                 b'(' => b')',
+                b'{' => b'}',
                 _ => {
                     cursor.advance();
                     continue;
@@ -54,12 +55,12 @@ impl PreProcessor for Ruby {
                     }
 
                     // Start of a nested bracket
-                    b'[' | b'(' => {
+                    b'[' | b'(' | b'{' => {
                         bracket_stack.push(cursor.curr);
                     }
 
                     // End of a nested bracket
-                    b']' | b')' if !bracket_stack.is_empty() => {
+                    b']' | b')' | b'}' if !bracket_stack.is_empty() => {
                         if !bracket_stack.pop(cursor.curr) {
                             // Unbalanced
                             cursor.advance();
@@ -98,6 +99,12 @@ mod tests {
                 "%w[flex data-[state=pending]:bg-[#0088cc] flex-col]",
                 "%w flex data-[state=pending]:bg-[#0088cc] flex-col ",
             ),
+            // %w{…}
+            ("%w{flex px-2.5}", "%w flex px-2.5 "),
+            (
+                "%w{flex data-[state=pending]:bg-(--my-color) flex-col}",
+                "%w flex data-[state=pending]:bg-(--my-color) flex-col ",
+            ),
             // %w(…)
             ("%w(flex px-2.5)", "%w flex px-2.5 "),
             (
@@ -114,4 +121,36 @@ mod tests {
             Ruby::test(input, expected);
         }
     }
+
+    #[test]
+    fn test_ruby_extraction() {
+        for (input, expected) in [
+            // %w[…]
+            ("%w[flex px-2.5]", vec!["flex", "px-2.5"]),
+            ("%w[px-2.5 flex]", vec!["flex", "px-2.5"]),
+            ("%w[2xl:flex]", vec!["2xl:flex"]),
+            (
+                "%w[flex data-[state=pending]:bg-[#0088cc] flex-col]",
+                vec!["flex", "data-[state=pending]:bg-[#0088cc]", "flex-col"],
+            ),
+            // %w{…}
+            ("%w{flex px-2.5}", vec!["flex", "px-2.5"]),
+            ("%w{px-2.5 flex}", vec!["flex", "px-2.5"]),
+            ("%w{2xl:flex}", vec!["2xl:flex"]),
+            (
+                "%w{flex data-[state=pending]:bg-(--my-color) flex-col}",
+                vec!["flex", "data-[state=pending]:bg-(--my-color)", "flex-col"],
+            ),
+            // %w(…)
+            ("%w(flex px-2.5)", vec!["flex", "px-2.5"]),
+            ("%w(px-2.5 flex)", vec!["flex", "px-2.5"]),
+            ("%w(2xl:flex)", vec!["2xl:flex"]),
+            (
+                "%w(flex data-[state=pending]:bg-(--my-color) flex-col)",
+                vec!["flex", "data-[state=pending]:bg-(--my-color)", "flex-col"],
+            ),
+        ] {
+            Ruby::test_extract_contains(input, expected);
+        }
+    }
 }
diff --git a/crates/oxide/src/extractor/utility_machine.rs b/crates/oxide/src/extractor/utility_machine.rs
index 5f8c74aa7..26b7019c2 100644
--- a/crates/oxide/src/extractor/utility_machine.rs
+++ b/crates/oxide/src/extractor/utility_machine.rs
@@ -312,10 +312,7 @@ mod tests {
                     vec!["let", "classes", "true"],
                 ),
                 // Inside an object (no spaces, key)
-                (
-                    r#"let classes = {'{}':true};"#,
-                    vec!["let", "classes", "true"],
-                ),
+                (r#"let classes = {'{}':true};"#, vec!["let", "classes"]),
                 // Inside an object (value)
                 (
                     r#"let classes = { primary: '{}' };"#,