diff --git a/src/formats/docx/content.rs b/src/formats/docx/content.rs
index c5a7c18b..b45f21ac 100644
--- a/src/formats/docx/content.rs
+++ b/src/formats/docx/content.rs
@@ -501,6 +501,11 @@ impl<'a, 'b, 'e> InlineWalker<'a, 'b, 'e> {
                         self.push(Inline::Text { text, style });
                     }
                 }
+                "sym" => {
+                    if let Some(glyph) = super::symbols::checkbox(child) {
+                        self.push(Inline::Text { text: glyph.to_string(), style });
+                    }
+                }
                 "tab" | "ptab" => self.push(Inline::Text { text: " ".into(), style: Style::PLAIN }),
                 // Markdown has no pages or columns, but every w:br still
                 // separates the runs around it: dropping a page break
diff --git a/src/formats/docx/mod.rs b/src/formats/docx/mod.rs
index eee5317e..b6a2f5e5 100644
--- a/src/formats/docx/mod.rs
+++ b/src/formats/docx/mod.rs
@@ -6,6 +6,7 @@
 mod content;
 mod numbering;
 mod styles;
+mod symbols;
 
 use crate::error::ConvertError;
 use crate::model::{Document, Note, NoteKind};
@@ -247,6 +248,70 @@ mod tests {
         );
     }
 
+    #[test]
+    fn symbol_checkboxes_preserve_states_and_run_style() {
+        for (font, empty, checked) in [
+            ("Wingdings 2", "00A3", "0052"),
+            ("wingdings 2", "F0A3", "F052"),
+            ("Wingdings", "006F", "00FE"),
+            ("WINGDINGS", "F06F", "F0FE"),
+        ] {
+            let document = format!(
+                r#"<w:document {W}><w:body><w:p>
+                <w:r><w:rPr><w:b/></w:rPr><w:sym w:font="{font}" w:char="{checked}"/><w:t> yes</w:t></w:r>
+                <w:r><w:t xml:space="preserve"> </w:t><w:sym w:font="{font}" w:char="{empty}"/><w:t> no ☑</w:t></w:r>
+                </w:p></w:body></w:document>"#
+            );
+            let bytes = docx_parts(&[("word/document.xml", &document)]);
+            let doc = parse(&bytes).unwrap();
+            let Some(Block::Paragraph(inlines)) = doc.blocks.first() else { panic!() };
+            assert_eq!(crate::model::inlines_to_plain_text(inlines), "☑ yes □ no ☑");
+            assert_eq!(
+                crate::to_markdown_bytes(&bytes, crate::Format::Docx).unwrap().trim(),
+                "**☑ yes** □ no ☑"
+            );
+        }
+    }
+
+    #[test]
+    fn symbol_checkboxes_in_table_keep_unselected_option_separate() {
+        let document = format!(
+            r#"<w:document {W}><w:body><w:tbl><w:tr><w:tc>
+            <w:p><w:r><w:t>☑ Required, amount:</w:t></w:r></w:p>
+            <w:p><w:r><w:sym w:font="Wingdings 2" w:char="00A3"/><w:t>Not required</w:t></w:r></w:p>
+            </w:tc></w:tr></w:tbl></w:body></w:document>"#
+        );
+        let bytes = docx_parts(&[("word/document.xml", &document)]);
+        let markdown = crate::to_markdown_bytes(&bytes, crate::Format::Docx).unwrap();
+        assert!(markdown.contains("☑ Required, amount:<br>□Not required"), "{markdown}");
+    }
+
+    #[test]
+    fn unknown_or_malformed_symbols_do_not_invent_checkbox_states() {
+        for attrs in [
+            r#"w:font="Arial" w:char="0052""#,
+            r#"w:font="Wingdings 2" w:char="0001""#,
+            r#"w:font="Wingdings 2" w:char="not-hex""#,
+            r#"w:font="Wingdings 2" w:char="+00A3""#,
+            r#"w:font="Wingdings 2" w:char="000A3""#,
+            r#"w:font="Wingdings 2" w:char="""#,
+            r#"w:font="Wingdings 2" w:char="100A3""#,
+            r#"w:font="Wingdings 2""#,
+            r#"w:char="00A3""#,
+        ] {
+            let document = format!(
+                r#"<w:document {W}><w:body><w:p><w:r>
+                <w:t>before</w:t><w:sym {attrs}/><w:t>after</w:t>
+                </w:r></w:p></w:body></w:document>"#
+            );
+            let bytes = docx_parts(&[("word/document.xml", &document)]);
+            assert_eq!(
+                crate::to_markdown_bytes(&bytes, crate::Format::Docx).unwrap().trim(),
+                "beforeafter"
+            );
+        }
+    }
+
     #[test]
     fn unmarked_run_edge_whitespace_is_kept() {
         // Converters that never write xml:space carry inter-word spacing on
diff --git a/src/formats/docx/symbols.rs b/src/formats/docx/symbols.rs
new file mode 100644
index 00000000..d3e8adc0
--- /dev/null
+++ b/src/formats/docx/symbols.rs
@@ -0,0 +1,34 @@
+//! Font-specific checkbox glyphs stored as WordprocessingML w:sym elements.
+use crate::package::xml::{Element, ns};
+
+pub(super) fn checkbox(symbol: &Element) -> Option<char> {
+    let font = symbol.attr(ns::W, "font")?;
+    let value = symbol.attr(ns::W, "char")?;
+    // Reject signs and overlong values even when integer parsing accepts them.
+    if value.is_empty() || value.len() > 4 || !value.bytes().all(|b| b.is_ascii_hexdigit()) {
+        return None;
+    }
+    let code = u16::from_str_radix(value, 16).ok()?;
+    // Word stores legacy symbol-font codes both as bytes and in U+F000..F0FF.
+    let code = match code {
+        0xf000..=0xf0ff => code - 0xf000,
+        code => code,
+    };
+    if font.eq_ignore_ascii_case("Wingdings 2") {
+        match code {
+            0xa3 => Some('□'),
+            0x52 => Some('☑'),
+            _ => None,
+        }
+    } else if font.eq_ignore_ascii_case("Wingdings") {
+        match code {
+            0x6f => Some('□'),
+            0xfe => Some('☑'),
+            _ => None,
+        }
+    } else {
+        // Unknown font/code pairs are not Unicode checkbox states. Keep the
+        // existing unsupported-symbol behavior instead of inventing a value.
+        None
+    }
+}