diff --git a/changes/issue-5732-workaround-to-build-msi-on-apple-m1 b/changes/issue-5732-workaround-to-build-msi-on-apple-m1
new file mode 100644
index 0000000000..0d7552df94
--- /dev/null
+++ b/changes/issue-5732-workaround-to-build-msi-on-apple-m1
@@ -0,0 +1 @@
+* Implemented retries as a workaround for transient failures when building MSI packages on Apple M1.
diff --git a/cmd/fleetctl/package.go b/cmd/fleetctl/package.go
index a0cb77c07f..6045af1c09 100644
--- a/cmd/fleetctl/package.go
+++ b/cmd/fleetctl/package.go
@@ -7,6 +7,7 @@ import (
 	"io/ioutil"
 	"path/filepath"
 	"runtime"
+	"strings"
 	"time"
 
 	"github.com/fleetdm/fleet/v4/orbit/pkg/packaging"
@@ -220,11 +221,29 @@ func packageCommand() *cli.Command {
 				zlog.Logger = zerolog.Nop()
 			}
 
-			fmt.Println("Generating your osquery installer...")
-			path, err := buildFunc(opt)
+			const maxAttempts = 9 // see #5732
+			var (
+				attempts int
+				path     string
+				err      error
+			)
+			for attempts < maxAttempts {
+				attempts++
+
+				if attempts > 1 {
+					fmt.Printf("Generating your osquery installer [attempt %d/%d]...\n\n", attempts, maxAttempts)
+				} else {
+					fmt.Println("Generating your osquery installer...")
+				}
+				path, err = buildFunc(opt)
+				if err == nil || !shouldRetry(c.String("type"), opt, err) {
+					break
+				}
+			}
 			if err != nil {
 				return err
 			}
+
 			path, _ = filepath.Abs(path)
 			fmt.Printf(`
 Success! You generated an osquery installer at %s
@@ -241,6 +260,25 @@ To add other devices to Fleet, distribute this installer using Chef, Ansible, Ja
 	}
 }
 
+func shouldRetry(pkgType string, opt packaging.Options, err error) bool {
+	if pkgType != "msi" || runtime.GOOS != "darwin" || runtime.GOARCH != "arm64" {
+		return false
+	}
+
+	// building an MSI on macos M1, check if the error is one that should be retried
+	errStr := err.Error()
+	switch {
+	case strings.Contains(errStr, "package root files: heat failed"):
+		return true
+	case strings.Contains(errStr, "build package: candle failed"):
+		return true
+	case strings.Contains(errStr, "build package: light failed"):
+		return true
+	default:
+		return false
+	}
+}
+
 func checkPEMCertificate(path string) error {
 	cert, err := ioutil.ReadFile(path)
 	if err != nil {