diff --git a/Cargo.lock b/Cargo.lock
index e333a6631f..fb45198ee1 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -2477,6 +2477,7 @@ dependencies = [
  "miette 4.2.1",
  "nu-json",
  "num-format",
+ "regex",
  "serde",
  "serde_json",
  "sys-locale",
diff --git a/crates/nu-command/src/dataframe/values/nu_dataframe/between_values.rs b/crates/nu-command/src/dataframe/values/nu_dataframe/between_values.rs
index da52985edd..96a2b10118 100644
--- a/crates/nu-command/src/dataframe/values/nu_dataframe/between_values.rs
+++ b/crates/nu-command/src/dataframe/values/nu_dataframe/between_values.rs
@@ -366,7 +366,8 @@ pub(super) fn compute_series_single_value(
                 rhs_span: right.span()?,
             }),
         },
-        Operator::Contains => match &right {
+        // TODO: update this to do a regex match instead of a simple contains?
+        Operator::RegexMatch => match &right {
             Value::String { val, .. } => contains_series_pat(&lhs, val, lhs_span),
             _ => Err(ShellError::OperatorMismatch {
                 op_span: operator.span,
diff --git a/crates/nu-engine/src/eval.rs b/crates/nu-engine/src/eval.rs
index 1a38c553c5..d3d2241e49 100644
--- a/crates/nu-engine/src/eval.rs
+++ b/crates/nu-engine/src/eval.rs
@@ -405,13 +405,13 @@ pub fn eval_expression(
                     let rhs = eval_expression(engine_state, stack, rhs)?;
                     lhs.not_in(op_span, &rhs)
                 }
-                Operator::Contains => {
+                Operator::RegexMatch => {
                     let rhs = eval_expression(engine_state, stack, rhs)?;
-                    lhs.contains(op_span, &rhs)
+                    lhs.regex_match(op_span, &rhs, false)
                 }
-                Operator::NotContains => {
+                Operator::NotRegexMatch => {
                     let rhs = eval_expression(engine_state, stack, rhs)?;
-                    lhs.not_contains(op_span, &rhs)
+                    lhs.regex_match(op_span, &rhs, true)
                 }
                 Operator::Modulo => {
                     let rhs = eval_expression(engine_state, stack, rhs)?;
diff --git a/crates/nu-parser/src/parser.rs b/crates/nu-parser/src/parser.rs
index 42169cd874..35db9ec20f 100644
--- a/crates/nu-parser/src/parser.rs
+++ b/crates/nu-parser/src/parser.rs
@@ -3967,9 +3967,9 @@ pub fn parse_operator(
         b"<=" => Operator::LessThanOrEqual,
         b">" => Operator::GreaterThan,
         b">=" => Operator::GreaterThanOrEqual,
-        b"=~" => Operator::Contains,
+        b"=~" => Operator::RegexMatch,
         b"=^" => Operator::StartsWith,
-        b"!~" => Operator::NotContains,
+        b"!~" => Operator::NotRegexMatch,
         b"+" => Operator::Plus,
         b"-" => Operator::Minus,
         b"*" => Operator::Multiply,
diff --git a/crates/nu-parser/src/type_check.rs b/crates/nu-parser/src/type_check.rs
index 8d9cf20fa2..11a16d3ea6 100644
--- a/crates/nu-parser/src/type_check.rs
+++ b/crates/nu-parser/src/type_check.rs
@@ -283,7 +283,7 @@ pub fn math_result_type(
             },
             Operator::Equal => (Type::Bool, None),
             Operator::NotEqual => (Type::Bool, None),
-            Operator::Contains => match (&lhs.ty, &rhs.ty) {
+            Operator::RegexMatch => match (&lhs.ty, &rhs.ty) {
                 (Type::String, Type::String) => (Type::Bool, None),
                 (Type::Any, _) => (Type::Bool, None),
                 (_, Type::Any) => (Type::Bool, None),
@@ -301,7 +301,7 @@ pub fn math_result_type(
                     )
                 }
             },
-            Operator::NotContains => match (&lhs.ty, &rhs.ty) {
+            Operator::NotRegexMatch => match (&lhs.ty, &rhs.ty) {
                 (Type::String, Type::String) => (Type::Bool, None),
                 (Type::Any, _) => (Type::Bool, None),
                 (_, Type::Any) => (Type::Bool, None),
diff --git a/crates/nu-protocol/Cargo.toml b/crates/nu-protocol/Cargo.toml
index 8ceffd47db..0f9fb0b546 100644
--- a/crates/nu-protocol/Cargo.toml
+++ b/crates/nu-protocol/Cargo.toml
@@ -22,6 +22,7 @@ nu-json = { path = "../nu-json", version = "0.60.1"  }
 typetag = "0.1.8"
 num-format = "0.4.0"
 sys-locale = "0.2.0"
+regex = "1.5.4"
 
 [features]
 plugin = ["serde_json"]
diff --git a/crates/nu-protocol/src/ast/expression.rs b/crates/nu-protocol/src/ast/expression.rs
index b0e92fec7f..3fe59a1777 100644
--- a/crates/nu-protocol/src/ast/expression.rs
+++ b/crates/nu-protocol/src/ast/expression.rs
@@ -32,8 +32,8 @@ impl Expression {
                     Operator::Pow => 100,
                     Operator::Multiply | Operator::Divide | Operator::Modulo => 95,
                     Operator::Plus | Operator::Minus => 90,
-                    Operator::NotContains
-                    | Operator::Contains
+                    Operator::NotRegexMatch
+                    | Operator::RegexMatch
                     | Operator::StartsWith
                     | Operator::LessThan
                     | Operator::LessThanOrEqual
diff --git a/crates/nu-protocol/src/ast/operator.rs b/crates/nu-protocol/src/ast/operator.rs
index c01ccd39eb..9e18683ab3 100644
--- a/crates/nu-protocol/src/ast/operator.rs
+++ b/crates/nu-protocol/src/ast/operator.rs
@@ -11,8 +11,8 @@ pub enum Operator {
     GreaterThan,
     LessThanOrEqual,
     GreaterThanOrEqual,
-    Contains,
-    NotContains,
+    RegexMatch,
+    NotRegexMatch,
     Plus,
     Minus,
     Multiply,
@@ -33,8 +33,8 @@ impl Display for Operator {
             Operator::NotEqual => write!(f, "!="),
             Operator::LessThan => write!(f, "<"),
             Operator::GreaterThan => write!(f, ">"),
-            Operator::Contains => write!(f, "=~"),
-            Operator::NotContains => write!(f, "!~"),
+            Operator::RegexMatch => write!(f, "=~"),
+            Operator::NotRegexMatch => write!(f, "!~"),
             Operator::Plus => write!(f, "+"),
             Operator::Minus => write!(f, "-"),
             Operator::Multiply => write!(f, "*"),
diff --git a/crates/nu-protocol/src/value/mod.rs b/crates/nu-protocol/src/value/mod.rs
index 382f3685ba..bf712c4f7e 100644
--- a/crates/nu-protocol/src/value/mod.rs
+++ b/crates/nu-protocol/src/value/mod.rs
@@ -12,6 +12,7 @@ pub use from_value::FromValue;
 use indexmap::map::IndexMap;
 use num_format::{Locale, ToFormattedString};
 pub use range::*;
+use regex::Regex;
 use serde::{Deserialize, Serialize};
 pub use stream::*;
 use sys_locale::get_locale;
@@ -2029,17 +2030,38 @@ impl Value {
         }
     }
 
-    pub fn contains(&self, op: Span, rhs: &Value) -> Result<Value, ShellError> {
+    pub fn regex_match(&self, op: Span, rhs: &Value, invert: bool) -> Result<Value, ShellError> {
         let span = span(&[self.span()?, rhs.span()?]);
 
         match (self, rhs) {
-            (Value::String { val: lhs, .. }, Value::String { val: rhs, .. }) => Ok(Value::Bool {
-                val: lhs.contains(rhs),
-                span,
-            }),
-            (Value::CustomValue { val: lhs, span }, rhs) => {
-                lhs.operation(*span, Operator::Contains, op, rhs)
+            (
+                Value::String { val: lhs, .. },
+                Value::String {
+                    val: rhs,
+                    span: rhs_span,
+                },
+            ) => {
+                // We are leaving some performance on the table by compiling the regex every time.
+                // Small regexes compile in microseconds, and the simplicity of this approach currently
+                // outweighs the performance costs. Revisit this if it ever becomes a bottleneck.
+                let regex = Regex::new(rhs)
+                    .map_err(|e| ShellError::UnsupportedInput(format!("{e}"), *rhs_span))?;
+                let is_match = regex.is_match(lhs);
+                Ok(Value::Bool {
+                    val: if invert { !is_match } else { is_match },
+                    span,
+                })
             }
+            (Value::CustomValue { val: lhs, span }, rhs) => lhs.operation(
+                *span,
+                if invert {
+                    Operator::NotRegexMatch
+                } else {
+                    Operator::RegexMatch
+                },
+                op,
+                rhs,
+            ),
             _ => Err(ShellError::OperatorMismatch {
                 op_span: op,
                 lhs_ty: self.get_type(),
@@ -2071,27 +2093,6 @@ impl Value {
         }
     }
 
-    pub fn not_contains(&self, op: Span, rhs: &Value) -> Result<Value, ShellError> {
-        let span = span(&[self.span()?, rhs.span()?]);
-
-        match (self, rhs) {
-            (Value::String { val: lhs, .. }, Value::String { val: rhs, .. }) => Ok(Value::Bool {
-                val: !lhs.contains(rhs),
-                span,
-            }),
-            (Value::CustomValue { val: lhs, span }, rhs) => {
-                lhs.operation(*span, Operator::NotContains, op, rhs)
-            }
-            _ => Err(ShellError::OperatorMismatch {
-                op_span: op,
-                lhs_ty: self.get_type(),
-                lhs_span: self.span()?,
-                rhs_ty: rhs.get_type(),
-                rhs_span: rhs.span()?,
-            }),
-        }
-    }
-
     pub fn modulo(&self, op: Span, rhs: &Value) -> Result<Value, ShellError> {
         let span = span(&[self.span()?, rhs.span()?]);
 
diff --git a/src/tests.rs b/src/tests.rs
index a41fed6ea9..eb1575a035 100644
--- a/src/tests.rs
+++ b/src/tests.rs
@@ -9,6 +9,7 @@ mod test_math;
 mod test_modules;
 mod test_parser;
 mod test_ranges;
+mod test_regex;
 mod test_strings;
 mod test_table_operations;
 mod test_type_check;
diff --git a/src/tests/test_regex.rs b/src/tests/test_regex.rs
new file mode 100644
index 0000000000..0f26f7dfde
--- /dev/null
+++ b/src/tests/test_regex.rs
@@ -0,0 +1,82 @@
+use crate::tests::{fail_test, run_test, TestResult};
+
+#[test]
+fn contains() -> TestResult {
+    run_test(r#"'foobarbaz' =~ bar"#, "true")
+}
+
+#[test]
+fn contains_case_insensitive() -> TestResult {
+    run_test(r#"'foobarbaz' =~ '(?i)BaR'"#, "true")
+}
+
+#[test]
+fn not_contains() -> TestResult {
+    run_test(r#"'foobarbaz' !~ asdf"#, "true")
+}
+
+#[test]
+fn match_full_line() -> TestResult {
+    run_test(r#"'foobarbaz' =~ '^foobarbaz$'"#, "true")
+}
+
+#[test]
+fn not_match_full_line() -> TestResult {
+    run_test(r#"'foobarbaz' !~ '^foobarbaz$'"#, "false")
+}
+
+#[test]
+fn starts_with() -> TestResult {
+    run_test(r#"'foobarbaz' =~ '^foo'"#, "true")
+}
+
+#[test]
+fn not_starts_with() -> TestResult {
+    run_test(r#"'foobarbaz' !~ '^foo'"#, "false")
+}
+
+#[test]
+fn ends_with() -> TestResult {
+    run_test(r#"'foobarbaz' =~ 'baz$'"#, "true")
+}
+
+#[test]
+fn not_ends_with() -> TestResult {
+    run_test(r#"'foobarbaz' !~ 'baz$'"#, "false")
+}
+
+#[test]
+fn where_works() -> TestResult {
+    run_test(
+        r#"[{name: somefile.txt} {name: anotherfile.csv }] | where name =~ ^s | get name.0"#,
+        "somefile.txt",
+    )
+}
+
+#[test]
+fn where_not_works() -> TestResult {
+    run_test(
+        r#"[{name: somefile.txt} {name: anotherfile.csv }] | where name !~ ^s | get name.0"#,
+        "anotherfile.csv",
+    )
+}
+
+#[test]
+fn invalid_regex_fails() -> TestResult {
+    fail_test(r#"'foo' =~ '['"#, "regex parse error")
+}
+
+#[test]
+fn invalid_not_regex_fails() -> TestResult {
+    fail_test(r#"'foo' !~ '['"#, "regex parse error")
+}
+
+#[test]
+fn regex_on_int_fails() -> TestResult {
+    fail_test(r#"33 =~ foo"#, "Types mismatched")
+}
+
+#[test]
+fn not_regex_on_int_fails() -> TestResult {
+    fail_test(r#"33 !~ foo"#, "Types mismatched")
+}