diff --git a/CHANGELOG.md b/CHANGELOG.md
index 8e92a85b2ed..4e90bc11492 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -8,6 +8,7 @@
 * [FEATURE] Add per-tenant compaction window [#3129](https://github.com/grafana/tempo/pull/3129) (@zalegrala)
 * [BUGFIX] Include statusMessage intrinsic attribute in tag search. [#3084](https://github.com/grafana/tempo/pull/3084) (@rcrowe)
 * [ENHANCEMENT] Update poller to make use of previous results and reduce backend load. [#2652](https://github.com/grafana/tempo/pull/2652) (@zalegrala)
+* [ENHANCEMENT] Improve TraceQL regex performance in certain queries. [#3139](https://github.com/grafana/tempo/pull/3139) (@joe-elliott)
 
 ## v2.3.0 / 2023-10-30
 
diff --git a/pkg/traceql/ast.go b/pkg/traceql/ast.go
index ced59a785d0..b1343d67aa9 100644
--- a/pkg/traceql/ast.go
+++ b/pkg/traceql/ast.go
@@ -3,6 +3,7 @@ package traceql
 import (
 	"fmt"
 	"math"
+	"regexp"
 	"time"
 )
 
@@ -368,10 +369,12 @@ type BinaryOperation struct {
 	Op  Operator
 	LHS FieldExpression
 	RHS FieldExpression
+
+	compiledExpression *regexp.Regexp
 }
 
-func newBinaryOperation(op Operator, lhs FieldExpression, rhs FieldExpression) BinaryOperation {
-	return BinaryOperation{
+func newBinaryOperation(op Operator, lhs FieldExpression, rhs FieldExpression) *BinaryOperation {
+	return &BinaryOperation{
 		Op:  op,
 		LHS: lhs,
 		RHS: rhs,
@@ -381,7 +384,7 @@ func newBinaryOperation(op Operator, lhs FieldExpression, rhs FieldExpression) B
 // nolint: revive
 func (BinaryOperation) __fieldExpression() {}
 
-func (o BinaryOperation) impliedType() StaticType {
+func (o *BinaryOperation) impliedType() StaticType {
 	if o.Op.isBoolean() {
 		return TypeBoolean
 	}
@@ -396,7 +399,7 @@ func (o BinaryOperation) impliedType() StaticType {
 	return o.RHS.impliedType()
 }
 
-func (o BinaryOperation) referencesSpan() bool {
+func (o *BinaryOperation) referencesSpan() bool {
 	return o.LHS.referencesSpan() || o.RHS.referencesSpan()
 }
 
diff --git a/pkg/traceql/ast_conditions.go b/pkg/traceql/ast_conditions.go
index cb3c325cbdd..d723ae1deed 100644
--- a/pkg/traceql/ast_conditions.go
+++ b/pkg/traceql/ast_conditions.go
@@ -31,7 +31,7 @@ func (o SelectOperation) extractConditions(request *FetchSpansRequest) {
 	request.SecondPassConditions = append(request.SecondPassConditions, selectR.Conditions...)
 }
 
-func (o BinaryOperation) extractConditions(request *FetchSpansRequest) {
+func (o *BinaryOperation) extractConditions(request *FetchSpansRequest) {
 	// TODO we can further optimise this by attempting to execute every FieldExpression, if they only contain statics it should resolve
 	switch o.LHS.(type) {
 	case Attribute:
diff --git a/pkg/traceql/ast_execute.go b/pkg/traceql/ast_execute.go
index 4c0a36a2bbf..ae786ff89a3 100644
--- a/pkg/traceql/ast_execute.go
+++ b/pkg/traceql/ast_execute.go
@@ -319,7 +319,7 @@ func (a Aggregate) evaluate(input []*Spanset) (output []*Spanset, err error) {
 	return output, nil
 }
 
-func (o BinaryOperation) execute(span Span) (Static, error) {
+func (o *BinaryOperation) execute(span Span) (Static, error) {
 	lhs, err := o.LHS.execute(span)
 	if err != nil {
 		return NewStaticNil(), err
@@ -381,10 +381,22 @@ func (o BinaryOperation) execute(span Span) (Static, error) {
 	case OpNotEqual:
 		return NewStaticBool(!lhs.Equals(rhs)), nil
 	case OpRegex:
-		matched, err := regexp.MatchString(rhs.S, lhs.S)
+		if o.compiledExpression == nil {
+			o.compiledExpression, err = regexp.Compile(rhs.S)
+			if err != nil {
+				return NewStaticNil(), err
+			}
+		}
+		matched := o.compiledExpression.MatchString(lhs.S)
 		return NewStaticBool(matched), err
 	case OpNotRegex:
-		matched, err := regexp.MatchString(rhs.S, lhs.S)
+		if o.compiledExpression == nil {
+			o.compiledExpression, err = regexp.Compile(rhs.S)
+			if err != nil {
+				return NewStaticNil(), err
+			}
+		}
+		matched := o.compiledExpression.MatchString(lhs.S)
 		return NewStaticBool(!matched), err
 	case OpAnd:
 		return NewStaticBool(lhs.B && rhs.B), nil
diff --git a/pkg/traceql/ast_stringer.go b/pkg/traceql/ast_stringer.go
index b18c9be25ac..d908594c2ca 100644
--- a/pkg/traceql/ast_stringer.go
+++ b/pkg/traceql/ast_stringer.go
@@ -58,7 +58,7 @@ func (f ScalarFilter) String() string {
 	return binaryOp(f.op, f.lhs, f.rhs)
 }
 
-func (o BinaryOperation) String() string {
+func (o *BinaryOperation) String() string {
 	return binaryOp(o.Op, o.LHS, o.RHS)
 }
 
diff --git a/pkg/traceql/ast_validate.go b/pkg/traceql/ast_validate.go
index fb18ecc97b5..aeb9d4eff8a 100644
--- a/pkg/traceql/ast_validate.go
+++ b/pkg/traceql/ast_validate.go
@@ -1,6 +1,9 @@
 package traceql
 
-import "fmt"
+import (
+	"fmt"
+	"regexp"
+)
 
 // unsupportedError is returned for traceql features that are not yet supported.
 type unsupportedError struct {
@@ -156,7 +159,7 @@ func (f ScalarFilter) validate() error {
 	return nil
 }
 
-func (o BinaryOperation) validate() error {
+func (o *BinaryOperation) validate() error {
 	if err := o.LHS.validate(); err != nil {
 		return err
 	}
@@ -179,6 +182,14 @@ func (o BinaryOperation) validate() error {
 		return fmt.Errorf("illegal operation for the given types: %s", o.String())
 	}
 
+	// if this is a regex operator confirm the RHS is a valid regex
+	if o.Op == OpRegex || o.Op == OpNotRegex {
+		_, err := regexp.Compile(o.RHS.String())
+		if err != nil {
+			return fmt.Errorf("invalid regex: %s", o.RHS.String())
+		}
+	}
+
 	// this condition may not be possible to hit since it's not parseable.
 	// however, if we did somehow end up this situation, it would be good to return
 	// a reasonable error
diff --git a/pkg/traceql/test_examples.yaml b/pkg/traceql/test_examples.yaml
index a71c5c80dab..6949f1b3aa8 100644
--- a/pkg/traceql/test_examples.yaml
+++ b/pkg/traceql/test_examples.yaml
@@ -205,6 +205,9 @@ validate_fails:
   - '{ traceDuration > "test" }'
   - '{ rootServiceName = 1 }'
   - '{ rootName != 3.2 }'
+  # invalid regexes
+  - '{ span.foo =~ "[" }'
+  - '{ span.foo !~ "[" }'
   # unary operators - incorrect types
   - '{ -true }'
   - '{ -"foo" = "bar" }'