diff --git a/pkg/engine/engine.go b/pkg/engine/engine.go
index 839ad4a31..00b3d917a 100644
--- a/pkg/engine/engine.go
+++ b/pkg/engine/engine.go
@@ -330,6 +330,11 @@ func cleanupParseError(filename string, err error) error {
 	return fmt.Errorf("parse error at (%s): %s", string(location), errMsg)
 }
 
+type TraceableError struct {
+	location string
+	message  string
+}
+
 func cleanupExecError(filename string, err error) error {
 	if _, isExecError := err.(template.ExecError); !isExecError {
 		return err
@@ -349,8 +354,51 @@ func cleanupExecError(filename string, err error) error {
 	if len(parts) >= 2 {
 		return fmt.Errorf("execution error at (%s): %s", string(location), parts[1])
 	}
+	current := err
+	fileLocations := []TraceableError{}
+	for {
+		if current == nil {
+			break
+		}
+		tokens = strings.SplitN(current.Error(), ": ", 3)
+		location = tokens[1]
+		traceable := TraceableError{
+			location: location,
+			message:  current.Error(),
+		}
+		fileLocations = append(fileLocations, traceable)
+		current = errors.Unwrap(current)
+	}
+
+	prevMessage := ""
+	for i := len(fileLocations) - 1; i >= 0; i-- {
+		currentMsg := fileLocations[i].message
+		if i == len(fileLocations)-1 {
+			prevMessage = currentMsg
+			continue
+		}
+
+		if strings.Contains(currentMsg, prevMessage) {
+			fileLocations[i].message = strings.ReplaceAll(fileLocations[i].message, prevMessage, "")
+		}
+		prevMessage = currentMsg
+	}
+
+	for i := len(fileLocations) - 1; i >= 0; i-- {
+		if strings.Contains(fileLocations[i].message, fileLocations[i].location) {
+			fileLocations[i].message = strings.ReplaceAll(fileLocations[i].message, fileLocations[i].location, "")
+		}
+	}
+
+	finalErrorString := ""
+	for _, i := range fileLocations {
+		if i.message == "" {
+			continue
+		}
+		finalErrorString = finalErrorString + "\n" + i.location + " " + i.message
+	}
 
-	return err
+	return fmt.Errorf("%s\n\n\n\nError: %s", finalErrorString, err.Error())
 }
 
 func sortTemplates(tpls map[string]renderable) []string {
diff --git a/pkg/engine/engine_test.go b/pkg/engine/engine_test.go
index 68e0158fa..8445abf83 100644
--- a/pkg/engine/engine_test.go
+++ b/pkg/engine/engine_test.go
@@ -18,6 +18,8 @@ package engine
 
 import (
 	"fmt"
+	"github.com/stretchr/testify/assert"
+	"helm.sh/helm/v4/pkg/chart/v2/loader"
 	"path"
 	"strings"
 	"sync"
@@ -1301,6 +1303,25 @@ func TestRenderTplMissingKeyString(t *testing.T) {
 	}
 }
 
+func TestSometimesJesseJustBe(t *testing.T) {
+	c, _ := loader.Load("/home/jesse/code/camunda-platform-helm/charts/camunda-platform-8.5")
+
+	v, _ := chartutil.ReadValuesFile("/home/jesse/code/helm/values.yaml")
+	val, _ := chartutil.CoalesceValues(c, v)
+	vals := map[string]interface{}{
+		"Values": val.AsMap(),
+	}
+	out, err := Render(c, vals)
+
+	if err != nil {
+		t.Errorf("Failed to render templates: %s", err)
+	}
+	assert.NotNil(t, out)
+	data := strings.TrimSpace(out["jesse-subchart-values-hacktest/charts/keycloak/templates/ingress.yaml"])
+	fmt.Println(data)
+	assert.NotEmpty(t, data)
+}
+
 func TestRenderCustomTemplateFuncs(t *testing.T) {
 	// Create a chart with two templates that use custom functions
 	c := &chart.Chart{