diff --git a/x-pack/elastic-agent/.gitignore b/x-pack/elastic-agent/.gitignore
index 22e2de50947c..81ce70aa69b3 100644
--- a/x-pack/elastic-agent/.gitignore
+++ b/x-pack/elastic-agent/.gitignore
@@ -4,5 +4,6 @@ elastic-agent
 elastic-agent.dev.yml
 pkg/agent/operation/tests/scripts/short--1.0.yml
 pkg/agent/operation/tests/scripts/configurable-1.0-darwin-x86/configurable
+pkg/agent/operation/tests/scripts/servicable-1.0-darwin-x86/configurable
+pkg/agent/transpiler/tests/exec-1.0-darwin-x86_64/exec
 pkg/agent/application/fleet.yml
-pkg/core/plugin/operation/tests/scripts/configurable/1.0/configurable
diff --git a/x-pack/elastic-agent/CHANGELOG.next.asciidoc b/x-pack/elastic-agent/CHANGELOG.next.asciidoc
index e1804b614c98..805132d6bdcc 100644
--- a/x-pack/elastic-agent/CHANGELOG.next.asciidoc
+++ b/x-pack/elastic-agent/CHANGELOG.next.asciidoc
@@ -42,6 +42,7 @@
 - Fix issues with dynamic inputs and conditions {pull}23886[23886]
 - Fix bad substitution of API key. {pull}24036[24036]
 - Fix docker enrollment issue related to Fleet Server change. {pull}24155[24155]
+- Improve log on failure of Endpoint Security installation. {pull}24429[24429]
 
 ==== New features
 
diff --git a/x-pack/elastic-agent/magefile.go b/x-pack/elastic-agent/magefile.go
index 0149e7ea0bd4..2585b7269f24 100644
--- a/x-pack/elastic-agent/magefile.go
+++ b/x-pack/elastic-agent/magefile.go
@@ -192,16 +192,19 @@ func (Build) Clean() {
 // TestBinaries build the required binaries for the test suite.
 func (Build) TestBinaries() error {
 	p := filepath.Join("pkg", "agent", "operation", "tests", "scripts")
-
+	p2 := filepath.Join("pkg", "agent", "transpiler", "tests")
 	configurableName := "configurable"
 	serviceableName := "serviceable"
+	execName := "exec"
 	if runtime.GOOS == "windows" {
 		configurableName += ".exe"
 		serviceableName += ".exe"
+		execName += ".exe"
 	}
 	return combineErr(
 		RunGo("build", "-o", filepath.Join(p, "configurable-1.0-darwin-x86_64", configurableName), filepath.Join(p, "configurable-1.0-darwin-x86_64", "main.go")),
 		RunGo("build", "-o", filepath.Join(p, "serviceable-1.0-darwin-x86_64", serviceableName), filepath.Join(p, "serviceable-1.0-darwin-x86_64", "main.go")),
+		RunGo("build", "-o", filepath.Join(p2, "exec-1.0-darwin-x86_64", execName), filepath.Join(p2, "exec-1.0-darwin-x86_64", "main.go")),
 	)
 }
 
diff --git a/x-pack/elastic-agent/pkg/agent/program/supported.go b/x-pack/elastic-agent/pkg/agent/program/supported.go
index a6189687b2d8..f584060e1d3a 100644
--- a/x-pack/elastic-agent/pkg/agent/program/supported.go
+++ b/x-pack/elastic-agent/pkg/agent/program/supported.go
@@ -24,7 +24,7 @@ func init() {
 	// spec/heartbeat.yml
 	// spec/metricbeat.yml
 	// spec/packetbeat.yml
-	unpacked := packer.MustUnpack("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")
+	unpacked := packer.MustUnpack("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")
 	SupportedMap = make(map[string]Spec)
 
 	for f, v := range unpacked {
diff --git a/x-pack/elastic-agent/pkg/agent/transpiler/steps.go b/x-pack/elastic-agent/pkg/agent/transpiler/steps.go
index 3d52ccacb34d..7f9d0d9fd7fc 100644
--- a/x-pack/elastic-agent/pkg/agent/transpiler/steps.go
+++ b/x-pack/elastic-agent/pkg/agent/transpiler/steps.go
@@ -253,10 +253,21 @@ func (r *ExecFileStep) Execute(ctx context.Context, rootDir string) error {
 	}
 	if err != nil {
 		exitErr, ok := err.(*exec.ExitError)
-		if ok && exitErr.Stderr != nil && len(exitErr.Stderr) > 0 {
-			return fmt.Errorf("operation 'Exec' failed: %s", string(exitErr.Stderr))
+		if ok && exitErr.Stderr != nil {
+			errStr := strings.TrimSpace(string(exitErr.Stderr))
+			if len(errStr) > 0 {
+				return fmt.Errorf("operation 'Exec' failed (return code: %d): %s", exitErr.ExitCode(), errStr)
+			}
+		}
+		exitCode := 1
+		if ok {
+			exitCode = exitErr.ExitCode()
+		}
+		outStr := strings.TrimSpace(string(output))
+		if len(outStr) == 0 {
+			outStr = "(command had no output)"
 		}
-		return fmt.Errorf("operation 'Exec' failed: %s", string(output))
+		return fmt.Errorf("operation 'Exec' failed (return code: %d): %s", exitCode, outStr)
 	}
 	return nil
 }
diff --git a/x-pack/elastic-agent/pkg/agent/transpiler/steps_test.go b/x-pack/elastic-agent/pkg/agent/transpiler/steps_test.go
index d618b1e1993f..7a14e63c00d8 100644
--- a/x-pack/elastic-agent/pkg/agent/transpiler/steps_test.go
+++ b/x-pack/elastic-agent/pkg/agent/transpiler/steps_test.go
@@ -5,7 +5,9 @@
 package transpiler
 
 import (
+	"context"
 	"fmt"
+	"os"
 	"runtime"
 	"testing"
 
@@ -69,3 +71,67 @@ func TestIsSubpath(t *testing.T) {
 		})
 	}
 }
+
+func TestExecFile_Success(t *testing.T) {
+	pwd, err := os.Getwd()
+	if err != nil {
+		panic(err)
+	}
+	binaryPath := "tests/exec-1.0-darwin-x86_64/exec"
+	step := ExecFile(10, binaryPath, "-output=stdout", "-exitcode=0")
+	err = step.Execute(context.Background(), pwd)
+	if err != nil {
+		t.Fatal("command should not have errored")
+	}
+}
+
+func TestExecFile_StdErr(t *testing.T) {
+	pwd, err := os.Getwd()
+	if err != nil {
+		panic(err)
+	}
+	binaryPath := "tests/exec-1.0-darwin-x86_64/exec"
+	step := ExecFile(10, binaryPath, "-output=stderr", "-exitcode=15")
+	err = step.Execute(context.Background(), pwd)
+	if err == nil {
+		t.Fatal("command should have errored")
+	}
+	errMsg := "operation 'Exec' failed (return code: 15): message written to stderr"
+	if err.Error() != errMsg {
+		t.Fatalf("got unexpected error: %s", err)
+	}
+}
+
+func TestExecFile_StdOut(t *testing.T) {
+	pwd, err := os.Getwd()
+	if err != nil {
+		panic(err)
+	}
+	binaryPath := "tests/exec-1.0-darwin-x86_64/exec"
+	step := ExecFile(10, binaryPath, "-output=stdout", "-exitcode=16")
+	err = step.Execute(context.Background(), pwd)
+	if err == nil {
+		t.Fatal("command should have errored")
+	}
+	errMsg := "operation 'Exec' failed (return code: 16): message written to stdout"
+	if err.Error() != errMsg {
+		t.Fatalf("got unexpected error: %s", err)
+	}
+}
+
+func TestExecFile_NoOutput(t *testing.T) {
+	pwd, err := os.Getwd()
+	if err != nil {
+		panic(err)
+	}
+	binaryPath := "tests/exec-1.0-darwin-x86_64/exec"
+	step := ExecFile(10, binaryPath, "-no-output", "-exitcode=17")
+	err = step.Execute(context.Background(), pwd)
+	if err == nil {
+		t.Fatal("command should have errored")
+	}
+	errMsg := "operation 'Exec' failed (return code: 17): (command had no output)"
+	if err.Error() != errMsg {
+		t.Fatalf("got unexpected error: %s", err)
+	}
+}
diff --git a/x-pack/elastic-agent/pkg/agent/transpiler/tests/exec-1.0-darwin-x86_64/main.go b/x-pack/elastic-agent/pkg/agent/transpiler/tests/exec-1.0-darwin-x86_64/main.go
new file mode 100644
index 000000000000..be043c53ac96
--- /dev/null
+++ b/x-pack/elastic-agent/pkg/agent/transpiler/tests/exec-1.0-darwin-x86_64/main.go
@@ -0,0 +1,35 @@
+// Copyright Elasticsearch B.V. and/or licensed to Elasticsearch B.V. under one
+// or more contributor license agreements. Licensed under the Elastic License;
+// you may not use this file except in compliance with the Elastic License.
+
+package main
+
+import (
+	"flag"
+	"fmt"
+	"io"
+	"os"
+)
+
+func main() {
+	noOutput := flag.Bool("no-output", false, "disable output")
+	output := flag.String("output", "stderr", "output destination")
+	exitcode := flag.Int("exitcode", 0, "exit code")
+	flag.Parse()
+
+	if *noOutput {
+		os.Exit(*exitcode)
+	}
+
+	var dest io.Writer
+	if *output == "stdout" {
+		dest = os.Stdout
+	} else if *output == "stderr" {
+		dest = os.Stderr
+	} else {
+		panic("unknown destination")
+	}
+
+	fmt.Fprintf(dest, "message written to %s", *output)
+	os.Exit(*exitcode)
+}
diff --git a/x-pack/elastic-agent/spec/endpoint.yml b/x-pack/elastic-agent/spec/endpoint.yml
index 7265ba2e693b..b45a3d35648d 100644
--- a/x-pack/elastic-agent/spec/endpoint.yml
+++ b/x-pack/elastic-agent/spec/endpoint.yml
@@ -11,12 +11,16 @@ check_install:
     path: "endpoint-security"
     args:
     - "verify"
+    - "--log"
+    - "stderr"
     timeout: 30
 post_install:
 - exec_file:
     path: "endpoint-security"
     args:
     - "install"
+    - "--log"
+    - "stderr"
     - "--upgrade"
     - "--resources"
     - "endpoint-security-resources.zip"
@@ -26,6 +30,8 @@ pre_uninstall:
     path: "endpoint-security"
     args:
       - "uninstall"
+      - "--log"
+      - "stderr"
     timeout: 600
 rules:
 - fix_stream: {}