diff --git a/api/go.mod b/api/go.mod
index a5e1ac306..bda68d40e 100644
--- a/api/go.mod
+++ b/api/go.mod
@@ -13,7 +13,7 @@ require (
 	github.com/mitchellh/go-testing-interface v1.14.1
 	github.com/mitchellh/mapstructure v1.5.0
 	github.com/shoenig/test v0.6.6
-	golang.org/x/exp v0.0.0-20230108222341-4b8118a2686a
+	golang.org/x/exp v0.0.0-20230728194245-b0cb94b80691
 )
 
 require (
diff --git a/api/go.sum b/api/go.sum
index a9f09bd2c..8a826edf1 100644
--- a/api/go.sum
+++ b/api/go.sum
@@ -36,8 +36,8 @@ github.com/stretchr/testify v1.7.1/go.mod h1:6Fq8oRcR53rry900zMqJjRRixrwX3KX962/
 github.com/stretchr/testify v1.8.0/go.mod h1:yNjHg4UonilssWZ8iaSj1OCr/vHnekPRkoO+kdMU+MU=
 github.com/stretchr/testify v1.8.1 h1:w7B6lhMri9wdJUVmEZPGGhZzrYTPvgJArz7wNPgYKsk=
 github.com/stretchr/testify v1.8.1/go.mod h1:w2LPCIKwWwSfY2zedu0+kehJoqGctiVI29o6fzry7u4=
-golang.org/x/exp v0.0.0-20230108222341-4b8118a2686a h1:tlXy25amD5A7gOfbXdqCGN5k8ESEed/Ee1E5RcrYnqU=
-golang.org/x/exp v0.0.0-20230108222341-4b8118a2686a/go.mod h1:CxIveKay+FTh1D0yPZemJVgC/95VzuuOLq5Qi4xnoYc=
+golang.org/x/exp v0.0.0-20230728194245-b0cb94b80691 h1:/yRP+0AN7mf5DkD3BAI6TOFnd51gEoDEb8o35jIFtgw=
+golang.org/x/exp v0.0.0-20230728194245-b0cb94b80691/go.mod h1:FXUEEKJgO7OQYeo8N01OfiKP8RXMtf6e8aTskBGqWdc=
 gopkg.in/check.v1 v0.0.0-20161208181325-20d25e280405/go.mod h1:Co6ibVJAznAaIkqp8huTwlJQCZ016jof/cbN4VW5Yz0=
 gopkg.in/yaml.v3 v3.0.0-20200313102051-9f266ea9e77c/go.mod h1:K4uyk7z7BCEPqu6E+C64Yfv1cQ7kz7rIZviUmN+EgEM=
 gopkg.in/yaml.v3 v3.0.1 h1:fxVm/GzAzEWqLHuvctI91KS9hhNmmWOoWu0XTYJS7CA=
diff --git a/client/allocrunner/taskrunner/getter/params.go b/client/allocrunner/taskrunner/getter/params.go
index d2e1b8a23..29f1b5cba 100644
--- a/client/allocrunner/taskrunner/getter/params.go
+++ b/client/allocrunner/taskrunner/getter/params.go
@@ -109,13 +109,19 @@ func (p *parameters) Equal(o *parameters) bool {
 		return false
 	case p.TaskDir != o.TaskDir:
 		return false
-	case !maps.EqualFunc(p.Headers, o.Headers, slices.Equal[string]):
+	case !maps.EqualFunc(p.Headers, o.Headers, headersCompareFn):
 		return false
 	}
 
 	return true
 }
 
+func headersCompareFn(a []string, b []string) bool {
+	slices.Sort(a)
+	slices.Sort(b)
+	return slices.Equal(a, b)
+}
+
 const (
 	// stop privilege escalation via setuid/setgid
 	// https://github.com/hashicorp/nomad/issues/6176
diff --git a/client/allocrunner/taskrunner/getter/params_test.go b/client/allocrunner/taskrunner/getter/params_test.go
index 15f9b77c8..560767c8b 100644
--- a/client/allocrunner/taskrunner/getter/params_test.go
+++ b/client/allocrunner/taskrunner/getter/params_test.go
@@ -135,6 +135,14 @@ func TestParameters_Equal_headers(t *testing.T) {
 	// equal
 	must.Equal(t, p1, p2)
 
+	// equal
+	must.Equal(t, p1, &parameters{
+		Headers: map[string][]string{
+			"West": {"California"},
+			"East": {"Florida", "New York"},
+		},
+	})
+
 	// not equal
 	p2.Headers["East"] = []string{"New York"}
 	must.NotEqual(t, p1, p2)
diff --git a/nomad/job_endpoint_test.go b/nomad/job_endpoint_test.go
index cab6dec9e..79ba20506 100644
--- a/nomad/job_endpoint_test.go
+++ b/nomad/job_endpoint_test.go
@@ -267,8 +267,22 @@ func TestJobEndpoint_Register_NonOverlapping(t *testing.T) {
 			return false, fmt.Errorf("expected 2 allocs but found %d:\n%v", n, allocResp.Allocations)
 		}
 
-		slices.SortFunc(allocResp.Allocations, func(a, b *structs.AllocListStub) bool {
-			return a.CreateIndex < b.CreateIndex
+		slices.SortFunc(allocResp.Allocations, func(a, b *structs.AllocListStub) int {
+			var result int
+			// cmp(a, b) should return
+			//   a positive number when a > b
+			if a.CreateIndex > b.CreateIndex {
+				result = 1
+			}
+			//   a negative number when a < b,
+			if a.CreateIndex < b.CreateIndex {
+				result = -1
+			}
+			//   zero when a == b.
+			result = 0
+
+			// invert the comparison to sort descending.
+			return result * -1
 		})
 
 		if alloc.ID != allocResp.Allocations[0].ID {
diff --git a/nomad/state/state_store.go b/nomad/state/state_store.go
index 463486a3f..445849fd0 100644
--- a/nomad/state/state_store.go
+++ b/nomad/state/state_store.go
@@ -5521,8 +5521,18 @@ func (s *StateStore) pruneJobSubmissions(namespace, jobID string, txn *txn) erro
 	}
 
 	// sort by job modify index descending so we can just keep the first N
-	slices.SortFunc(stored, func(a, b lang.Pair[uint64, uint64]) bool {
-		return a.First > b.First
+	slices.SortFunc(stored, func(a, b lang.Pair[uint64, uint64]) int {
+		var cmp int = 0
+		if a.First < b.First {
+			cmp = -1
+		}
+		if a.First > b.First {
+			cmp = +1
+		}
+
+		// Convert the sort into a descending sort by inverting the sign
+		cmp = cmp * -1
+		return cmp
 	})
 
 	// remove the outdated submission versions