diff --git a/simulator/model/table.rs b/simulator/model/table.rs
index b7e1a6a32..98462394a 100644
--- a/simulator/model/table.rs
+++ b/simulator/model/table.rs
@@ -185,10 +185,58 @@ impl From<ast::Literal> for SimValue {
     }
 }
 
-/// Sanitaizes a string literal by removing single quote at front and back
-/// and escaping double single quotes
-fn sanitize_string(input: &str) -> String {
-    input[1..input.len() - 1].replace("''", "'").to_string()
+/// Converts a SQL string literal with already-escaped single quotes to a regular string by:
+/// - Removing the enclosing single quotes
+/// - Converting sequences of 2N single quotes ('''''') to N single quotes (''')
+///
+/// Assumes:
+/// - The input starts and ends with a single quote
+/// - The input contains a valid amount of single quotes inside the enclosing quotes;
+///   i.e. any ' is escaped as a double ''
+fn unescape_singlequotes(input: &str) -> String {
+    assert!(
+        input.starts_with('\'') && input.ends_with('\''),
+        "Input string must be wrapped in single quotes"
+    );
+    // Skip first and last characters (the enclosing quotes)
+    let inner = &input[1..input.len() - 1];
+
+    let mut result = String::with_capacity(inner.len());
+    let mut chars = inner.chars().peekable();
+
+    while let Some(c) = chars.next() {
+        if c == '\'' {
+            // Count consecutive single quotes
+            let mut quote_count = 1;
+            while chars.peek() == Some(&'\'') {
+                quote_count += 1;
+                chars.next();
+            }
+            assert!(
+                quote_count % 2 == 0,
+                "Expected even number of quotes, got {} in string {}",
+                quote_count,
+                input
+            );
+            // For every pair of quotes, output one quote
+            for _ in 0..(quote_count / 2) {
+                result.push('\'');
+            }
+        } else {
+            result.push(c);
+        }
+    }
+
+    result
+}
+
+/// Escapes a string by doubling contained single quotes and then wrapping it in single quotes.
+fn escape_singlequotes(input: &str) -> String {
+    let mut result = String::with_capacity(input.len() + 2);
+    result.push('\'');
+    result.push_str(&input.replace("'", "''"));
+    result.push('\'');
+    result
 }
 
 impl From<&ast::Literal> for SimValue {
@@ -196,8 +244,7 @@ impl From<&ast::Literal> for SimValue {
         let new_value = match value {
             ast::Literal::Null => types::Value::Null,
             ast::Literal::Numeric(number) => Numeric::from(number).into(),
-            // TODO: see how to avoid sanitizing here
-            ast::Literal::String(string) => types::Value::build_text(sanitize_string(string)),
+            ast::Literal::String(string) => types::Value::build_text(unescape_singlequotes(string)),
             ast::Literal::Blob(blob) => types::Value::Blob(
                 blob.as_bytes()
                     .chunks_exact(2)
@@ -227,7 +274,7 @@ impl From<&SimValue> for ast::Literal {
             types::Value::Null => Self::Null,
             types::Value::Integer(i) => Self::Numeric(i.to_string()),
             types::Value::Float(f) => Self::Numeric(f.to_string()),
-            text @ types::Value::Text(..) => Self::String(format!("'{}'", text)),
+            text @ types::Value::Text(..) => Self::String(escape_singlequotes(&text.to_string())),
             types::Value::Blob(blob) => Self::Blob(hex::encode(blob)),
         }
     }
@@ -266,3 +313,32 @@ impl From<&limbo_core::types::Value> for SimValue {
         Self(value.clone())
     }
 }
+
+#[cfg(test)]
+mod tests {
+    use crate::model::table::{escape_singlequotes, unescape_singlequotes};
+
+    #[test]
+    fn test_unescape_singlequotes() {
+        assert_eq!(unescape_singlequotes("'hello'"), "hello");
+        assert_eq!(unescape_singlequotes("'O''Reilly'"), "O'Reilly");
+        assert_eq!(
+            unescape_singlequotes("'multiple''single''quotes'"),
+            "multiple'single'quotes"
+        );
+        assert_eq!(unescape_singlequotes("'test''''test'"), "test''test");
+        assert_eq!(unescape_singlequotes("'many''''''quotes'"), "many'''quotes");
+    }
+
+    #[test]
+    fn test_escape_singlequotes() {
+        assert_eq!(escape_singlequotes("hello"), "'hello'");
+        assert_eq!(escape_singlequotes("O'Reilly"), "'O''Reilly'");
+        assert_eq!(
+            escape_singlequotes("multiple'single'quotes"),
+            "'multiple''single''quotes'"
+        );
+        assert_eq!(escape_singlequotes("test''test"), "'test''''test'");
+        assert_eq!(escape_singlequotes("many'''quotes"), "'many''''''quotes'");
+    }
+}