diff --git a/internal/search/query/transformer.go b/internal/search/query/transformer.go
index 07f23c4c36a..1d620a43b89 100644
--- a/internal/search/query/transformer.go
+++ b/internal/search/query/transformer.go
@@ -1,12 +1,9 @@
 package query
 
 import (
-	"fmt"
 	"strconv"
 	"strings"
 
-	"github.com/grafana/regexp"
-
 	"github.com/sourcegraph/sourcegraph/lib/errors"
 )
 
@@ -691,8 +688,12 @@ func ExperimentalPhraseBoost(originalQuery string, basic Basic) Basic {
 
 	// Check if the pattern is a single top-level AND expression with no negated or regexp clauses.
 	switch p := basic.Pattern.(type) {
+	case Pattern:
+		if !p.Annotation.Labels.IsSet(Quoted) || p.Negated || p.Annotation.Labels.IsSet(Regexp) {
+			return basic
+		}
 	case Operator:
-		if p.Kind != And || len(p.Operands) <= 1 {
+		if p.Kind != And {
 			return basic
 		}
 		for _, child := range p.Operands {
@@ -714,14 +715,12 @@ func ExperimentalPhraseBoost(originalQuery string, basic Basic) Basic {
 	}
 
 	query := strings.Join(filteredTerms, " ")
-	pattern := fmt.Sprintf(`(^|\b)%s($|\b)`, regexp.QuoteMeta(query))
-
 	basic.Pattern = Operator{
 		Kind: Or,
 		Operands: []Node{
 			Pattern{
-				Value:      pattern,
-				Annotation: Annotation{Labels: Boost | Regexp | Standard},
+				Value:      query,
+				Annotation: Annotation{Labels: Boost | Literal | Standard},
 			},
 			basic.Pattern,
 		},
diff --git a/internal/search/query/transformer_test.go b/internal/search/query/transformer_test.go
index 70da14457a0..ad88bf515f3 100644
--- a/internal/search/query/transformer_test.go
+++ b/internal/search/query/transformer_test.go
@@ -23,28 +23,31 @@ func TestExperimentalPhraseBoost(t *testing.T) {
 	}
 
 	// expect phrase query
-	autogold.Expect(`(or "(^|\\b)foo bar bas($|\\b)" (and "foo" "bar" "bas"))`).Equal(t, test("foo bar bas", SearchTypeKeyword))
-	autogold.Expect(`(or "(^|\\b)\\(foo and bar\\) and bas($|\\b)" (and "foo" "bar" "bas"))`).Equal(t, test("(foo and bar) and bas", SearchTypeKeyword))
-	autogold.Expect(`(or "(^|\\b)\\* int func\\(($|\\b)" (and "*" "int" "func("))`).Equal(t, test("* int func(", SearchTypeKeyword))
-	autogold.Expect(`(or "(^|\\b)\"foo bar\" bas qux($|\\b)" (and "foo bar" "bas" "qux"))`).Equal(t, test(`"foo bar" bas qux`, SearchTypeKeyword))
-	autogold.Expect(`(or "(^|\\b)foo 'bar bas' qux($|\\b)" (and "foo" "bar bas" "qux"))`).Equal(t, test(`foo 'bar bas' qux`, SearchTypeKeyword))
+	autogold.Expect(`(or "foo bar bas" (and "foo" "bar" "bas"))`).Equal(t, test("foo bar bas", SearchTypeKeyword))
+	autogold.Expect(`(or "(foo and bar) and bas" (and "foo" "bar" "bas"))`).Equal(t, test("(foo and bar) and bas", SearchTypeKeyword))
+	autogold.Expect(`(or "* int func(" (and "*" "int" "func("))`).Equal(t, test("* int func(", SearchTypeKeyword))
+	autogold.Expect(`(or "\"foo bar\" bas qux" (and "foo bar" "bas" "qux"))`).Equal(t, test(`"foo bar" bas qux`, SearchTypeKeyword))
+	autogold.Expect(`(or "foo 'bar bas' qux" (and "foo" "bar bas" "qux"))`).Equal(t, test(`foo 'bar bas' qux`, SearchTypeKeyword))
 
 	// expect no phrase query
 	autogold.Expect(`"foo bar bas"`).Equal(t, test("/foo bar bas/", SearchTypeKeyword))
 	autogold.Expect(`(and "foo" "bar" "ba.*")`).Equal(t, test("foo bar /ba.*/", SearchTypeKeyword))
 	autogold.Expect(`"foo"`).Equal(t, test("foo", SearchTypeKeyword))
-	autogold.Expect(`(or "(^|\\b)foo and bar($|\\b)" (and "foo" "bar"))`).Equal(t, test("foo and bar", SearchTypeKeyword))
+	autogold.Expect(`(or "foo and bar" (and "foo" "bar"))`).Equal(t, test("foo and bar", SearchTypeKeyword))
 	autogold.Expect(`(and "foo" (not "bar"))`).Equal(t, test("foo not bar", SearchTypeKeyword))
 	autogold.Expect(`(and "foo" "bar" (not "bas") "quz")`).Equal(t, test("foo bar not bas quz", SearchTypeKeyword))
 	autogold.Expect(`(or "foo" "bar" "bas")`).Equal(t, test("foo or bar or bas", SearchTypeKeyword))
 	autogold.Expect(`(or (and "foo" "bar") (and "quz" "biz"))`).Equal(t, test("foo and bar or (quz and biz)", SearchTypeKeyword))
 
 	// cases that came up in user feedback
-	autogold.Expect(`(and "repo:golang/go" (or "(^|\\b)// The vararg opts parameter can include functions to configure the($|\\b)" (and "//" "The" "vararg" "opts" "parameter" "can" "include" "functions" "to" "configure" "the")))`).Equal(t, test("repo:golang/go // The vararg opts parameter can include functions to configure the", SearchTypeKeyword))
-	autogold.Expect(`(and "context:global" (or "(^|\\b)invalid modelID;($|\\b)" (and "invalid" "modelID;")))`).Equal(t, test("context:global invalid modelID;", SearchTypeKeyword))
-	autogold.Expect(`(and "context:global" (or "(^|\\b)return \"various\";($|\\b)" (and "return" "\"various\";")))`).Equal(t, test("context:global return \"various\";", SearchTypeKeyword))
-	autogold.Expect(`(and "repo:golang/go" (or "(^|\\b)test server($|\\b)" (and "test" "server")))`).Equal(t, test("repo:golang/go test server", SearchTypeKeyword))
-	autogold.Expect(`(and "repo:sourcegraph/cody@main" (or "(^|\\b)the models and other($|\\b)" (and "the" "models" "other")))`).Equal(t, test("repo:sourcegraph/cody@main the models and other ", SearchTypeKeyword))
+	autogold.Expect(`(and "repo:golang/go" (or "// The vararg opts parameter can include functions to configure the" (and "//" "The" "vararg" "opts" "parameter" "can" "include" "functions" "to" "configure" "the")))`).Equal(t, test("repo:golang/go // The vararg opts parameter can include functions to configure the", SearchTypeKeyword))
+	autogold.Expect(`(and "context:global" (or "invalid modelID;" (and "invalid" "modelID;")))`).Equal(t, test("context:global invalid modelID;", SearchTypeKeyword))
+	autogold.Expect(`(and "context:global" (or "return \"various\";" (and "return" "\"various\";")))`).Equal(t, test("context:global return \"various\";", SearchTypeKeyword))
+	autogold.Expect(`(and "repo:golang/go" (or "test server" (and "test" "server")))`).Equal(t, test("repo:golang/go test server", SearchTypeKeyword))
+	autogold.Expect(`(and "repo:sourcegraph/cody@main" (or "the models and other" (and "the" "models" "other")))`).Equal(t, test("repo:sourcegraph/cody@main the models and other ", SearchTypeKeyword))
+	autogold.Expect(`(and "repo:sourcegraph/cody@main" (or "'sourcegraph'" "sourcegraph"))`).Equal(t, test("repo:sourcegraph/cody@main 'sourcegraph'", SearchTypeKeyword))
+	autogold.Expect(`(and "repo:sourcegraph/zoekt" (or "\"some string\"" "some string"))`).Equal(t, test("repo:sourcegraph/zoekt \"some string\"", SearchTypeKeyword))
+
 }
 
 func TestSubstituteAliases(t *testing.T) {