diff --git a/pkg/kapp/resourcesmisc/custom_waiting_resource.go b/pkg/kapp/resourcesmisc/custom_waiting_resource.go
index 110ea5689..f3d8065e5 100644
--- a/pkg/kapp/resourcesmisc/custom_waiting_resource.go
+++ b/pkg/kapp/resourcesmisc/custom_waiting_resource.go
@@ -65,10 +65,16 @@ func (s CustomWaitingResource) IsDoneApplying() DoneApplyState {
 	}
 
 	if s.waitRule.Ytt != nil {
+		startTime, found := timeoutMap.Load(s.resource.Description())
+		if !found {
+			timeoutMap.Store(s.resource.Description(), time.Now().Unix())
+		}
 		configObj, err := WaitRuleContractV1{
 			ResourceMatcher: ctlres.AnyMatcher{
 				Matchers: ctlconf.ResourceMatchers(s.waitRule.ResourceMatchers).AsResourceMatchers()},
-			Starlark: s.waitRule.Ytt.FuncContractV1.Resource,
+			Starlark:    s.waitRule.Ytt.FuncContractV1.Resource,
+			CurrentTime: time.Now().Unix(),
+			StartTime:   startTime.(int64),
 		}.Apply(s.resource)
 		if err != nil {
 			return DoneApplyState{Done: true, Successful: false, Message: fmt.Sprintf(
@@ -99,8 +105,8 @@ func (s CustomWaitingResource) IsDoneApplying() DoneApplyState {
 					isTimeOutConditionPresent = true
 					if s.hasTimeoutOccurred(condMatcher.Timeout, s.resource.Description()) {
 						return DoneApplyState{Done: true, Successful: false, Message: fmt.Sprintf(
-							"Encountered failure condition %s == %s: %s (message: %s) continuously for %s duration",
-							cond.Type, condMatcher.Status, cond.Reason, cond.Message, condMatcher.Timeout)}
+							"continuously failed for %s with %s == %s: %s (message: %s)",
+							condMatcher.Timeout, cond.Type, condMatcher.Status, cond.Reason, cond.Message)}
 					}
 					return DoneApplyState{Done: false, Message: fmt.Sprintf(
 						"%s: %s (message: %s)",
diff --git a/pkg/kapp/resourcesmisc/wait_rule_contract_v1.go b/pkg/kapp/resourcesmisc/wait_rule_contract_v1.go
index e1344d9ac..077247eeb 100644
--- a/pkg/kapp/resourcesmisc/wait_rule_contract_v1.go
+++ b/pkg/kapp/resourcesmisc/wait_rule_contract_v1.go
@@ -16,6 +16,8 @@ import (
 type WaitRuleContractV1 struct {
 	ResourceMatcher ctlres.ResourceMatcher
 	Starlark        string
+	CurrentTime     int64
+	StartTime       int64
 }
 
 type waitRuleContractV1Result struct {
@@ -48,6 +50,7 @@ func (t WaitRuleContractV1) evalYtt(res ctlres.Resource) (*WaitRuleContractV1Res
 		}
 		return yaml.Marshal(res.DeepCopyRaw())
 	}
+	opts.DataValuesFlags.KVsFromStrings = []string{fmt.Sprintf("startTime=%d", t.StartTime), fmt.Sprintf("currentTime=%d", t.CurrentTime)}
 
 	filesToProcess := []*files.File{
 		files.MustNewFileFromSource(files.NewBytesSource("resource.star", []byte(t.Starlark))),
diff --git a/test/e2e/wait_timeout_test.go b/test/e2e/wait_timeout_test.go
index b6b4ccecb..515222791 100644
--- a/test/e2e/wait_timeout_test.go
+++ b/test/e2e/wait_timeout_test.go
@@ -103,7 +103,7 @@ waitRules:
 			RunOpts{IntoNs: true, AllowError: true, StdinReader: strings.NewReader(fmt.Sprintf(yaml2, "nginx:200"))})
 
 		require.Error(t, err)
-		require.Contains(t, err.Error(), "message: containers with unready status: [nginx]) continuously for 50s duration")
+		require.Contains(t, err.Error(), "Continuously failed for 50s with")
 	})
 
 	cleanUp()