diff --git a/changes/issue-5504-improve-debug-output b/changes/issue-5504-improve-debug-output
new file mode 100644
index 0000000000..d71a96e1c5
--- /dev/null
+++ b/changes/issue-5504-improve-debug-output
@@ -0,0 +1 @@
+* Improve the output of `fleetclt debug errors` and add the ability to print the errors to stdout via the `-stdout` flag.
diff --git a/cmd/fleetctl/debug.go b/cmd/fleetctl/debug.go
index 80a7f00d94..ac90eedf0f 100644
--- a/cmd/fleetctl/debug.go
+++ b/cmd/fleetctl/debug.go
@@ -22,6 +22,9 @@ import (
 	"github.com/urfave/cli/v2"
 )
 
+// Defining here for testing purposes
+var nowFn = time.Now
+
 func debugCommand() *cli.Command {
 	return &cli.Command{
 		Name:  "debug",
@@ -58,7 +61,11 @@ func writeFile(filename string, bytes []byte, mode os.FileMode) error {
 }
 
 func outfileName(name string) string {
-	return fmt.Sprintf("fleet-%s-%s", name, time.Now().Format(time.RFC3339))
+	return fmt.Sprintf("fleet-%s-%s", name, nowFn().Format(time.RFC3339))
+}
+
+func outfileNameWithExt(name string, ext string) string {
+	return fmt.Sprintf("%s.%s", outfileName(name), ext)
 }
 
 func debugProfileCommand() *cli.Command {
@@ -285,11 +292,10 @@ func debugArchiveCommand() *cli.Command {
 				"db-process-list",
 			}
 
-			outpath := getOutfile(c)
-			if outpath == "" {
-				outpath = outfileName("profiles-archive")
+			outfile := getOutfile(c)
+			if outfile == "" {
+				outfile = outfileNameWithExt("profiles-archive", "tar.gz")
 			}
-			outfile := outpath + ".tar.gz"
 
 			f, err := secure.OpenFile(outfile, os.O_CREATE|os.O_WRONLY, defaultFileMode)
 			if err != nil {
@@ -334,7 +340,7 @@ func debugArchiveCommand() *cli.Command {
 
 				if err := tarwriter.WriteHeader(
 					&tar.Header{
-						Name: outpath + "/" + profile,
+						Name: outfile + "/" + profile,
 						Size: int64(len(res)),
 						Mode: defaultFileMode,
 					},
@@ -347,7 +353,14 @@ func debugArchiveCommand() *cli.Command {
 				}
 			}
 
-			fmt.Fprintf(os.Stderr, "Archive written to %s\n", outfile)
+			fmt.Fprintf(os.Stderr, "################################################################################\n"+
+				"# WARNING:\n"+
+				"#   The files in the generated archive may contain sensitive data.\n"+
+				"#   Please review them before sharing.\n"+
+				"#\n"+
+				"#   Archive written to: %s\n"+
+				"################################################################################\n",
+				outfile)
 
 			return nil
 		},
@@ -530,6 +543,7 @@ func debugErrorsCommand() *cli.Command {
 			configFlag(),
 			contextFlag(),
 			debugFlag(),
+			stdoutFlag(),
 		},
 		Action: func(c *cli.Context) error {
 			fleet, err := clientFromCLI(c)
@@ -538,23 +552,45 @@ func debugErrorsCommand() *cli.Command {
 			}
 
 			outfile := getOutfile(c)
-			if outfile == "" {
-				outfile = outfileName(name)
+			stdout := getStdout(c)
+
+			if stdout && outfile != "" {
+				return errors.New("-stdout and -outfile must not be specified together")
 			}
 
-			f, err := os.OpenFile(outfile, os.O_WRONLY|os.O_CREATE|os.O_TRUNC, defaultFileMode)
-			if err != nil {
-				return err
-			}
-			defer f.Close()
+			out := os.Stdout
 
-			if err := fleet.DebugErrors(f); err != nil {
+			if !stdout {
+				if outfile == "" {
+					outfile = outfileNameWithExt(name, "json")
+				}
+
+				f, err := os.OpenFile(outfile, os.O_WRONLY|os.O_CREATE|os.O_TRUNC, defaultFileMode)
+				if err != nil {
+					return err
+				}
+				defer f.Close()
+				out = f
+			}
+
+			if err := fleet.DebugErrors(out); err != nil {
 				return err
 			}
-			if err := f.Close(); err != nil {
-				return fmt.Errorf("write errors to file: %w", err)
+
+			if !stdout {
+				if err := out.Close(); err != nil {
+					return fmt.Errorf("write errors to file: %w", err)
+				}
+
+				fmt.Fprintf(os.Stderr, "################################################################################\n"+
+					"# WARNING:\n"+
+					"#   The generated file may contain sensitive data.\n"+
+					"#   Please review the file before sharing.\n"+
+					"#\n"+
+					"#   Output written to: %s\n"+
+					"################################################################################\n",
+					outfile)
 			}
-			fmt.Fprintf(os.Stderr, "Output written to %s\n", outfile)
 
 			return nil
 		},
diff --git a/cmd/fleetctl/debug_test.go b/cmd/fleetctl/debug_test.go
index a3c7468571..22458cf93c 100644
--- a/cmd/fleetctl/debug_test.go
+++ b/cmd/fleetctl/debug_test.go
@@ -19,6 +19,7 @@ import (
 	"time"
 
 	"github.com/fleetdm/fleet/v4/server/fleet"
+	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"
 )
 
@@ -200,3 +201,21 @@ func TestDebugResolveHostname(t *testing.T) {
 	err = resolveHostname(context.Background(), timeout, noSuchHost)
 	require.Error(t, err)
 }
+
+func TestFilenameFunctions(t *testing.T) {
+	nowFn = func() time.Time {
+		now, _ := time.Parse(time.RFC3339, "1969-06-19T21:44:05Z")
+		return now
+	}
+	defer func() { nowFn = time.Now }()
+
+	t.Run("outfileName builds a file name using the name provided + current time ", func(t *testing.T) {
+		name := outfileName("test")
+		assert.Equal(t, name, "fleet-test-1969-06-19T21:44:05Z")
+	})
+
+	t.Run("outfileNameWithExt builds a file name using the name and extension provided + current time ", func(t *testing.T) {
+		name := outfileNameWithExt("test", "go")
+		assert.Equal(t, name, "fleet-test-1969-06-19T21:44:05Z.go")
+	})
+}
diff --git a/cmd/fleetctl/flags.go b/cmd/fleetctl/flags.go
index 3d264842ea..c6a7679276 100644
--- a/cmd/fleetctl/flags.go
+++ b/cmd/fleetctl/flags.go
@@ -6,6 +6,7 @@ const (
 	outfileFlagName          = "outfile"
 	debugFlagName            = "debug"
 	fleetCertificateFlagName = "fleet-certificate"
+	stdoutFlagName           = "stdout"
 )
 
 func outfileFlag() cli.Flag {
@@ -44,3 +45,15 @@ func fleetCertificateFlag() cli.Flag {
 func getFleetCertificate(c *cli.Context) string {
 	return c.String(fleetCertificateFlagName)
 }
+
+func stdoutFlag() cli.Flag {
+	return &cli.BoolFlag{
+		Name:    stdoutFlagName,
+		EnvVars: []string{"STDOUT"},
+		Usage:   "Print contents to stdout",
+	}
+}
+
+func getStdout(c *cli.Context) bool {
+	return c.Bool(stdoutFlagName)
+}
diff --git a/cmd/fleetctl/get.go b/cmd/fleetctl/get.go
index b77ef177f2..7943a81f4e 100644
--- a/cmd/fleetctl/get.go
+++ b/cmd/fleetctl/get.go
@@ -24,7 +24,6 @@ const (
 	jsonFlagName                = "json"
 	withQueriesFlagName         = "with-queries"
 	expiredFlagName             = "expired"
-	stdoutFlagName              = "stdout"
 	includeServerConfigFlagName = "include-server-config"
 )
 
@@ -753,10 +752,7 @@ func getCarveCommand() *cli.Command {
 		Name:  "carve",
 		Usage: "Retrieve details for a carve by ID",
 		Flags: []cli.Flag{
-			&cli.BoolFlag{
-				Name:  stdoutFlagName,
-				Usage: "Print carve contents to stdout",
-			},
+			stdoutFlag(),
 			configFlag(),
 			contextFlag(),
 			outfileFlag(),