diff --git a/crates/red_knot_python_semantic/src/types/infer.rs b/crates/red_knot_python_semantic/src/types/infer.rs
index 4b3bf4af42..9f805edf6f 100644
--- a/crates/red_knot_python_semantic/src/types/infer.rs
+++ b/crates/red_knot_python_semantic/src/types/infer.rs
@@ -1426,13 +1426,14 @@ impl<'db> TypeInferenceBuilder<'db> {
     }
 
     fn infer_string_literal_expression(&mut self, literal: &ast::ExprStringLiteral) -> Type<'db> {
-        let value = if literal.value.len() <= Self::MAX_STRING_LITERAL_SIZE {
-            literal.value.to_str().into()
+        if literal.value.len() <= Self::MAX_STRING_LITERAL_SIZE {
+            Type::StringLiteral(StringLiteralType::new(
+                self.db,
+                literal.value.to_str().into(),
+            ))
         } else {
-            Box::default()
-        };
-
-        Type::StringLiteral(StringLiteralType::new(self.db, value))
+            Type::LiteralString
+        }
     }
 
     fn infer_bytes_literal_expression(&mut self, literal: &ast::ExprBytesLiteral) -> Type<'db> {
@@ -2041,13 +2042,23 @@ impl<'db> TypeInferenceBuilder<'db> {
             }
 
             (Type::StringLiteral(lhs), Type::StringLiteral(rhs), ast::Operator::Add) => {
-                Type::StringLiteral(StringLiteralType::new(self.db, {
-                    let lhs_value = lhs.value(self.db).to_string();
-                    let rhs_value = rhs.value(self.db).as_ref();
-                    (lhs_value + rhs_value).into()
-                }))
+                let lhs_value = lhs.value(self.db).to_string();
+                let rhs_value = rhs.value(self.db).as_ref();
+                if lhs_value.len() + rhs_value.len() <= Self::MAX_STRING_LITERAL_SIZE {
+                    Type::StringLiteral(StringLiteralType::new(self.db, {
+                        (lhs_value + rhs_value).into()
+                    }))
+                } else {
+                    Type::LiteralString
+                }
             }
 
+            (
+                Type::StringLiteral(_) | Type::LiteralString,
+                Type::StringLiteral(_) | Type::LiteralString,
+                ast::Operator::Add,
+            ) => Type::LiteralString,
+
             (Type::StringLiteral(s), Type::IntLiteral(n), ast::Operator::Mult)
             | (Type::IntLiteral(n), Type::StringLiteral(s), ast::Operator::Mult) => {
                 if n < 1 {
@@ -2066,6 +2077,15 @@ impl<'db> TypeInferenceBuilder<'db> {
                 }
             }
 
+            (Type::LiteralString, Type::IntLiteral(n), ast::Operator::Mult)
+            | (Type::IntLiteral(n), Type::LiteralString, ast::Operator::Mult) => {
+                if n < 1 {
+                    Type::StringLiteral(StringLiteralType::new(self.db, Box::default()))
+                } else {
+                    Type::LiteralString
+                }
+            }
+
             _ => Type::Unknown, // TODO
         }
     }
@@ -2892,6 +2912,70 @@ mod tests {
         Ok(())
     }
 
+    #[test]
+    fn multiplied_literal_string() -> anyhow::Result<()> {
+        let mut db = setup_db();
+        let content = format!(
+            r#"
+        v = "{y}"
+        w = 10*"{y}"
+        x = "{y}"*10
+        z = 0*"{y}"
+        u = (-100)*"{y}"
+        "#,
+            y = "a".repeat(TypeInferenceBuilder::MAX_STRING_LITERAL_SIZE + 1),
+        );
+        db.write_dedented("src/a.py", &content)?;
+
+        assert_public_ty(&db, "src/a.py", "v", "LiteralString");
+        assert_public_ty(&db, "src/a.py", "w", "LiteralString");
+        assert_public_ty(&db, "src/a.py", "x", "LiteralString");
+        assert_public_ty(&db, "src/a.py", "z", r#"Literal[""]"#);
+        assert_public_ty(&db, "src/a.py", "u", r#"Literal[""]"#);
+        Ok(())
+    }
+
+    #[test]
+    fn truncated_string_literals_become_literal_string() -> anyhow::Result<()> {
+        let mut db = setup_db();
+        let content = format!(
+            r#"
+        w = "{y}"
+        x = "a" + "{z}"
+        "#,
+            y = "a".repeat(TypeInferenceBuilder::MAX_STRING_LITERAL_SIZE + 1),
+            z = "a".repeat(TypeInferenceBuilder::MAX_STRING_LITERAL_SIZE),
+        );
+        db.write_dedented("src/a.py", &content)?;
+
+        assert_public_ty(&db, "src/a.py", "w", "LiteralString");
+        assert_public_ty(&db, "src/a.py", "x", "LiteralString");
+
+        Ok(())
+    }
+
+    #[test]
+    fn adding_string_literals_and_literal_string() -> anyhow::Result<()> {
+        let mut db = setup_db();
+        let content = format!(
+            r#"
+        v = "{y}"
+        w = "{y}" + "a"
+        x = "a" + "{y}"
+        z = "{y}" + "{y}"
+        "#,
+            y = "a".repeat(TypeInferenceBuilder::MAX_STRING_LITERAL_SIZE + 1),
+        );
+        db.write_dedented("src/a.py", &content)?;
+
+        assert_public_ty(&db, "src/a.py", "v", "LiteralString");
+        assert_public_ty(&db, "src/a.py", "w", "LiteralString");
+        assert_public_ty(&db, "src/a.py", "x", "LiteralString");
+        assert_public_ty(&db, "src/a.py", "z", "LiteralString");
+
+        Ok(())
+    }
+
     #[test]
     fn bytes_type() -> anyhow::Result<()> {
         let mut db = setup_db();