diff --git a/polars/polars-ops/src/chunked_array/strings/namespace.rs b/polars/polars-ops/src/chunked_array/strings/namespace.rs
index 360b37706958..1643540af7e5 100644
--- a/polars/polars-ops/src/chunked_array/strings/namespace.rs
+++ b/polars/polars-ops/src/chunked_array/strings/namespace.rs
@@ -8,7 +8,7 @@ use polars_arrow::export::arrow::compute::substring::substring;
 use polars_arrow::export::arrow::{self};
 use polars_arrow::kernels::string::*;
 use polars_core::export::num::Num;
-use polars_core::export::regex::{escape, Regex};
+use polars_core::export::regex::{escape, NoExpand, Regex};
 
 use super::*;
 #[cfg(feature = "string_encoding")]
@@ -207,8 +207,8 @@ pub trait Utf8NameSpaceImpl: AsUtf8 {
     /// Replace the leftmost regex-matched (sub)string with another string; take
     /// fast-path for small (<= 32 chars) strings (otherwise regex faster).
     fn replace<'a>(&'a self, pat: &str, val: &str) -> PolarsResult<Utf8Chunked> {
-        let lit = pat.chars().all(|c| !c.is_ascii_punctuation());
-        let ca = self.as_utf8();
+        let lit = !(pat.chars().any(|c| c.is_ascii_punctuation())
+            | val.chars().any(|c| c.is_ascii_punctuation()));
         let reg = Regex::new(pat)?;
         let f = |s: &'a str| {
             if lit && (s.len() <= 32) {
@@ -217,25 +217,36 @@ pub trait Utf8NameSpaceImpl: AsUtf8 {
                 reg.replace(s, val)
             }
         };
+        let ca = self.as_utf8();
         Ok(ca.apply(f))
     }
 
     /// Replace the leftmost literal (sub)string with another string
-    fn replace_literal(&self, pat: &str, val: &str) -> PolarsResult<Utf8Chunked> {
-        self.replace(escape(pat).as_str(), val)
+    fn replace_literal<'a>(&'a self, pat: &str, val: &str) -> PolarsResult<Utf8Chunked> {
+        let reg = Regex::new(escape(pat).as_str())?;
+        let f = |s: &'a str| {
+            if s.len() <= 32 {
+                Cow::Owned(s.replacen(pat, val, 1))
+            } else {
+                reg.replace(s, NoExpand(val))
+            }
+        };
+        let ca = self.as_utf8();
+        Ok(ca.apply(f))
     }
 
     /// Replace all regex-matched (sub)strings with another string
     fn replace_all(&self, pat: &str, val: &str) -> PolarsResult<Utf8Chunked> {
         let ca = self.as_utf8();
         let reg = Regex::new(pat)?;
-        let f = |s| reg.replace_all(s, val);
-        Ok(ca.apply(f))
+        Ok(ca.apply(|s| reg.replace_all(s, val)))
     }
 
     /// Replace all matching literal (sub)strings with another string
     fn replace_literal_all(&self, pat: &str, val: &str) -> PolarsResult<Utf8Chunked> {
-        self.replace_all(escape(pat).as_str(), val)
+        let ca = self.as_utf8();
+        let reg = Regex::new(escape(pat).as_str())?;
+        Ok(ca.apply(|s| reg.replace_all(s, NoExpand(val))))
     }
 
     /// Extract the nth capture group from pattern
diff --git a/py-polars/tests/unit/namespaces/test_string.py b/py-polars/tests/unit/namespaces/test_string.py
index 366b24ac12ae..312f8b043359 100644
--- a/py-polars/tests/unit/namespaces/test_string.py
+++ b/py-polars/tests/unit/namespaces/test_string.py
@@ -299,6 +299,13 @@ def test_replace() -> None:
         (r"^\(", "[", True, ["* * text", "(with) special\n * chars **etc...?$"]),
         (r"t$", "an", False, ["* * texan", "(with) special\n * chars **etc...?$"]),
         (r"t$", "an", True, ["* * text", "(with) special\n * chars **etc...?$"]),
+        (r"(with) special", "$1", True, ["* * text", "$1\n * chars **etc...?$"]),
+        (
+            r"\((with)\) special",
+            ":$1:",
+            False,
+            ["* * text", ":with:\n * chars **etc...?$"],
+        ),
     ):
         # series
         assert (
@@ -315,23 +322,38 @@ def test_replace() -> None:
             )["text"].to_list()
         )
 
+    assert pl.Series(["."]).str.replace(".", "$0", literal=True)[0] == "$0"
+    assert pl.Series(["(.)(?)"]).str.replace(".", "$1", literal=True)[0] == "($1)(?)"
+
 
 def test_replace_all() -> None:
     df = pl.DataFrame(
-        data=[(1, "* * text"), (2, "(with) special * chars **etc...?$")],
+        data=[(1, "* * text"), (2, "(with) special\n * chars **etc...?$")],
         schema=["idx", "text"],
         orient="row",
     )
     for pattern, replacement, as_literal, expected in (
-        (r"\*", "-", False, ["- - text", "(with) special - chars --etc...?$"]),
-        (r"*", "-", True, ["- - text", "(with) special - chars --etc...?$"]),
+        (r"\*", "-", False, ["- - text", "(with) special\n - chars --etc...?$"]),
+        (r"*", "-", True, ["- - text", "(with) special\n - chars --etc...?$"]),
         (r"\W", "", False, ["text", "withspecialcharsetc"]),
-        (r".?$", "", True, ["* * text", "(with) special * chars **etc.."]),
+        (r".?$", "", True, ["* * text", "(with) special\n * chars **etc.."]),
+        (
+            r"(with) special",
+            "$1",
+            True,
+            ["* * text", "$1\n * chars **etc...?$"],
+        ),
+        (
+            r"\((with)\) special",
+            ":$1:",
+            False,
+            ["* * text", ":with:\n * chars **etc...?$"],
+        ),
         (
             r"(\b)[\w\s]{2,}(\b)",
             "$1(blah)$3",
             False,
-            ["* * (blah)", "((blah)) (blah) * (blah) **(blah)...?$"],
+            ["* * (blah)", "((blah)) (blah)\n * (blah) **(blah)...?$"],
         ),
     ):
         # series
@@ -352,6 +374,15 @@ def test_replace_all() -> None:
         with pytest.raises(pl.ComputeError):
             df["text"].str.replace_all("*", "")
 
+    assert (
+        pl.Series([r"(.)(\?)(\?)"]).str.replace_all("\?", "$0", literal=True)[0]
+        == "(.)($0)($0)"
+    )
+    assert (
+        pl.Series([r"(.)(\?)(\?)"]).str.replace_all("\?", "$0", literal=False)[0]
+        == "(.)(\?)(\?)"
+    )
+
 
 def test_replace_expressions() -> None:
     df = pl.DataFrame({"foo": ["123 bla 45 asd", "xyz 678 910t"], "value": ["A", "B"]})