diff --git a/crates/bashkit/src/interpreter/mod.rs b/crates/bashkit/src/interpreter/mod.rs
index f36b208f..8eb4642e 100644
--- a/crates/bashkit/src/interpreter/mod.rs
+++ b/crates/bashkit/src/interpreter/mod.rs
@@ -9749,4 +9749,30 @@ echo "count=$COUNT"
             .unwrap();
         assert_eq!(result.stdout.trim(), "match");
     }
+
+    #[tokio::test]
+    async fn test_assoc_array_in_double_quotes() {
+        // Issue #399: ${arr["key"]} inside double quotes misparsed
+        let mut bash = crate::Bash::new();
+        let result = bash
+            .exec(r#"declare -A arr; arr["foo"]="bar"; echo "value: ${arr["foo"]}""#)
+            .await
+            .unwrap();
+        assert_eq!(result.stdout.trim(), "value: bar");
+    }
+
+    #[tokio::test]
+    async fn test_assoc_array_keys_in_quotes() {
+        // Issue #399: ${!arr[@]} in string context
+        let mut bash = crate::Bash::new();
+        let result = bash
+            .exec(r#"declare -A arr; arr["a"]=1; arr["b"]=2; echo "keys: ${!arr[@]}""#)
+            .await
+            .unwrap();
+        let output = result.stdout.trim();
+        // Keys may be in any order
+        assert!(output.starts_with("keys: "), "got: {}", output);
+        assert!(output.contains("a"), "got: {}", output);
+        assert!(output.contains("b"), "got: {}", output);
+    }
 }
diff --git a/crates/bashkit/src/parser/lexer.rs b/crates/bashkit/src/parser/lexer.rs
index 793554e1..0c92d81b 100644
--- a/crates/bashkit/src/parser/lexer.rs
+++ b/crates/bashkit/src/parser/lexer.rs
@@ -1043,6 +1043,12 @@ impl<'a> Lexer<'a> {
                         content.push('(');
                         self.advance();
                         self.read_command_subst_into(&mut content);
+                    } else if self.peek_char() == Some('{') {
+                        // ${...} parameter expansion — track brace depth so
+                        // inner quotes (e.g. ${arr["key"]}) don't end the string
+                        content.push('{');
+                        self.advance();
+                        self.read_param_expansion_into(&mut content);
                     }
                 }
                 '`' => {
@@ -1170,6 +1176,82 @@ impl<'a> Lexer<'a> {
         }
     }
 
+    /// Read parameter expansion content after `${`, handling nested braces and quotes.
+    /// In bash, quotes inside `${...}` (e.g. `${arr["key"]}`) don't terminate the
+    /// outer double-quoted string. Appends chars including closing `}` to `content`.
+    fn read_param_expansion_into(&mut self, content: &mut String) {
+        let mut depth = 1;
+        while let Some(c) = self.peek_char() {
+            match c {
+                '{' => {
+                    depth += 1;
+                    content.push(c);
+                    self.advance();
+                }
+                '}' => {
+                    depth -= 1;
+                    self.advance();
+                    content.push('}');
+                    if depth == 0 {
+                        break;
+                    }
+                }
+                '"' => {
+                    // Quotes inside ${...} are part of the expansion, not string delimiters
+                    content.push('"');
+                    self.advance();
+                }
+                '\'' => {
+                    content.push('\'');
+                    self.advance();
+                }
+                '\\' => {
+                    // Inside ${...} within double quotes, same escape rules apply:
+                    // \", \\, \$, \` produce the escaped char; others keep backslash
+                    self.advance();
+                    if let Some(esc) = self.peek_char() {
+                        match esc {
+                            '"' | '\\' | '$' | '`' => {
+                                content.push(esc);
+                                self.advance();
+                            }
+                            '}' => {
+                                // \} should be a literal } without closing the expansion
+                                content.push('\\');
+                                content.push('}');
+                                self.advance();
+                            }
+                            _ => {
+                                content.push('\\');
+                                content.push(esc);
+                                self.advance();
+                            }
+                        }
+                    } else {
+                        content.push('\\');
+                    }
+                }
+                '$' => {
+                    content.push('$');
+                    self.advance();
+                    if self.peek_char() == Some('(') {
+                        content.push('(');
+                        self.advance();
+                        self.read_command_subst_into(content);
+                    } else if self.peek_char() == Some('{') {
+                        content.push('{');
+                        self.advance();
+                        self.read_param_expansion_into(content);
+                    }
+                }
+                _ => {
+                    content.push(c);
+                    self.advance();
+                }
+            }
+        }
+    }
+
     /// Check if the content starting with { looks like a brace expansion
     /// Brace expansion: {a,b,c} or {1..5} (contains , or ..)
     /// Brace group: { cmd; } (contains spaces, semicolons, newlines)
diff --git a/crates/bashkit/src/parser/mod.rs b/crates/bashkit/src/parser/mod.rs
index 3270f0d6..48cd36ad 100644
--- a/crates/bashkit/src/parser/mod.rs
+++ b/crates/bashkit/src/parser/mod.rs
@@ -2389,6 +2389,12 @@ impl<'a> Parser<'a> {
                                 }
                                 index.push(chars.next().unwrap());
                             }
+                            // Strip surrounding quotes from index (e.g. "foo" -> foo)
+                            if (index.starts_with('"') && index.ends_with('"'))
+                                || (index.starts_with('\'') && index.ends_with('\''))
+                            {
+                                index = index[1..index.len() - 1].to_string();
+                            }
                             // After ], check for operators on array subscripts
                             if let Some(&next_c) = chars.peek() {
                                 if next_c == ':' && (index == "@" || index == "*") {