diff --git a/docs/development/roadmap.md b/docs/development/roadmap.md
index 32a9c64..54362fe 100644
--- a/docs/development/roadmap.md
+++ b/docs/development/roadmap.md
@@ -52,7 +52,7 @@
     - [x] Inline code
     - [x] Lists
         - [ ] Nested lists
-    - [ ] Checkboxes
+    - [x] Checkboxes
         - [ ] Move this roadmap to en
 - [ ] Full-text search
 - [ ] Begin centralizing state
diff --git a/src/syntax/content/parser/context/block.rs b/src/syntax/content/parser/context/block.rs
index 608b58b..11fa54f 100644
--- a/src/syntax/content/parser/context/block.rs
+++ b/src/syntax/content/parser/context/block.rs
@@ -9,8 +9,7 @@ use crate::{
             lexeme::Lexeme,
             state::State,
             token::{
-                Token, header::Header, preformat::PreFormat,
-                paragraph::Paragraph, literal::Literal, list::List, item::Item,
+                Token, checkbox::CheckBox, header::Header, item::Item, list::List, literal::Literal, paragraph::Paragraph, preformat::PreFormat
             },
         },
     },
@@ -98,7 +97,13 @@ pub fn parse(
             }
         },
         Block::Item(ordered) => {
-            if Item::probe_end(lexeme) {
+            if CheckBox::probe(lexeme) {
+                log!("Probed CheckBox: {lexeme}");
+                tokens.push(Token::CheckBox(CheckBox::lex(lexeme)));
+                iterator.next();
+                iterator.next();
+                return true
+            } else if Item::probe_end(lexeme) {
                 tokens.push(Token::Item(Item::new(false)));
                 log!("Block Context: Item -> List on {lexeme}");
                 state.context.block = Block::List(ordered);
diff --git a/src/syntax/content/parser/segment.rs b/src/syntax/content/parser/segment.rs
index 26fdec1..28cfdb1 100644
--- a/src/syntax/content/parser/segment.rs
+++ b/src/syntax/content/parser/segment.rs
@@ -17,7 +17,7 @@ pub mod delimiter {
             Delimiters {
                 atomic: vec!['`', '|', '\\'],
                 double: vec!['_', '~'],
-                flanking: vec!['_', '*', '~', '(', ')', '\'', '"'],
+                flanking: vec!['_', '*', '~', '(', ')', '[', ']', '\'', '"'],
                 punctuation: vec![',', '.', ';', ':', '?', '!'],
                 whitespace: vec!['\n', ' '],
             }
diff --git a/src/syntax/content/parser/token.rs b/src/syntax/content/parser/token.rs
index fb88989..9cead7c 100644
--- a/src/syntax/content/parser/token.rs
+++ b/src/syntax/content/parser/token.rs
@@ -2,6 +2,7 @@ use crate::syntax::content::Parseable as _;
 
 pub mod anchor;
 pub mod bold;
+pub mod checkbox;
 pub mod code;
 pub mod header;
 pub mod item;
@@ -19,6 +20,7 @@ pub mod underline;
 pub enum Token {
     Anchor(anchor::Anchor),
     Bold(bold::Bold),
+    CheckBox(checkbox::CheckBox),
     Code(code::Code),
     Strike(strike::Strike),
     Header(header::Header),
@@ -38,6 +40,7 @@ impl Token {
         match *self {
             Token::Anchor(ref d) => d.render(),
             Token::Bold(ref d) => d.render(),
+            Token::CheckBox(ref d) => d.render(),
             Token::Code(ref d) => d.render(),
             Token::Strike(ref d) => d.render(),
             Token::Header(ref d) => d.render(),
@@ -59,6 +62,7 @@ impl std::fmt::Display for Token {
         let data = match *self {
             Token::Anchor(ref d) => format!("{d}"),
             Token::Bold(ref d) => format!("{d}"),
+            Token::CheckBox(ref d) => format!("{d}"),
             Token::Code(ref d) => format!("{d}"),
             Token::Strike(ref d) => format!("{d}"),
             Token::Header(ref d) => format!("{d}"),
diff --git a/src/syntax/content/parser/token/checkbox.rs b/src/syntax/content/parser/token/checkbox.rs
new file mode 100644
index 0000000..ebdafcd
--- /dev/null
+++ b/src/syntax/content/parser/token/checkbox.rs
@@ -0,0 +1,61 @@
+use crate::{
+    syntax::content::{Parseable, Lexeme},
+};
+
+#[derive(Debug, Clone, Eq, PartialEq)]
+pub struct CheckBox {
+    checked: bool,
+}
+
+impl CheckBox {
+    pub fn new(checked: bool) -> CheckBox {
+        CheckBox { checked }
+    }
+}
+
+impl Parseable for CheckBox {
+    fn probe(lexeme: &Lexeme) -> bool {
+        lexeme.match_triple_as_char(('[', ' ', ']'))
+        || lexeme.match_triple_as_char(('[', 'x', ']'))
+    }
+
+    fn lex(lexeme: &Lexeme) -> CheckBox {
+        use crate::prelude::*;
+        log!("Lexing: {lexeme}");
+        if lexeme.match_next_as_char('x') {
+            CheckBox::new(true)
+        } else {
+            CheckBox::new(false)
+        }
+    }
+
+    fn render(&self) -> String {
+        let toggle = if self.checked {
+            " checked "
+        } else {
+            ""
+        };
+        format!(r#"<input type="checkbox"{toggle}/>"#)
+    }
+}
+
+impl std::fmt::Display for CheckBox {
+    fn fmt(&self, f: &mut std::fmt::Formatter) -> std::fmt::Result {
+        let display_state = if self.checked { "checked" } else { "empty" };
+        write!(f, "CheckBox [{display_state}]")
+    }
+}
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+
+    #[test]
+    fn render() {
+        let code_open = CheckBox::new(true);
+        assert_eq!(code_open.render(), r#"<input type="checkbox" checked />"#);
+
+        let code_closed = CheckBox::new(false);
+        assert_eq!(code_closed.render(), r#"<input type="checkbox"/>"#);
+    }
+}