diff --git a/ee/debug/checkups/checkups.go b/ee/debug/checkups/checkups.go
index 71c3886c0..374ca539f 100644
--- a/ee/debug/checkups/checkups.go
+++ b/ee/debug/checkups/checkups.go
@@ -108,7 +108,7 @@ func checkupsFor(k types.Knapsack, target targetBits) []checkupInt {
 		{&enrollSecretCheckup{k: k}, doctorSupported | flareSupported},
 		{&bboltdbCheckup{k: k}, flareSupported},
 		{&networkCheckup{}, doctorSupported | flareSupported},
-		{&installCheckup{}, flareSupported},
+		{&installCheckup{k: k}, flareSupported},
 		{&servicesCheckup{}, doctorSupported | flareSupported},
 		{&powerCheckup{}, flareSupported},
 		{&osqueryCheckup{k: k}, doctorSupported | flareSupported},
diff --git a/ee/debug/checkups/install.go b/ee/debug/checkups/install.go
index 3c5ed90bd..01b1837d4 100644
--- a/ee/debug/checkups/install.go
+++ b/ee/debug/checkups/install.go
@@ -7,10 +7,11 @@ import (
 	"io"
 	"runtime"
 
-	"github.com/kolide/launcher/pkg/launcher"
+	"github.com/kolide/launcher/ee/agent/types"
 )
 
 type installCheckup struct {
+	k types.Knapsack
 }
 
 func (i *installCheckup) Name() string {
@@ -25,7 +26,7 @@ func (i *installCheckup) Run(ctx context.Context, extraWriter io.Writer) error {
 		return fmt.Errorf("gathering installation logs: %w", err)
 	}
 
-	if err := gatherInstallerInfo(extraZip); err != nil {
+	if err := gatherInstallerInfo(extraZip, i.k.Identifier()); err != nil {
 		return fmt.Errorf("gathering installer info: %w", err)
 	}
 
@@ -56,14 +57,3 @@ func gatherInstallationLogs(z *zip.Writer) error {
 
 	return addFileToZip(z, "/var/log/install.log")
 }
-
-func gatherInstallerInfo(z *zip.Writer) error {
-	if runtime.GOOS == "windows" {
-		return nil
-	}
-
-	configDir := launcher.DefaultPath(launcher.EtcDirectory)
-	installerInfoPath := fmt.Sprintf("%s/installer-info.json", configDir)
-
-	return addFileToZip(z, installerInfoPath)
-}
diff --git a/ee/debug/checkups/install_other.go b/ee/debug/checkups/install_other.go
new file mode 100644
index 000000000..ad86f05b8
--- /dev/null
+++ b/ee/debug/checkups/install_other.go
@@ -0,0 +1,18 @@
+//go:build !windows
+// +build !windows
+
+package checkups
+
+import (
+	"archive/zip"
+	"fmt"
+
+	"github.com/kolide/launcher/pkg/launcher"
+)
+
+func gatherInstallerInfo(z *zip.Writer, _ string) error {
+	configDir := launcher.DefaultPath(launcher.EtcDirectory)
+	installerInfoPath := fmt.Sprintf("%s/installer-info.json", configDir)
+
+	return addFileToZip(z, installerInfoPath)
+}
diff --git a/ee/debug/checkups/install_windows.go b/ee/debug/checkups/install_windows.go
new file mode 100644
index 000000000..286ce29fe
--- /dev/null
+++ b/ee/debug/checkups/install_windows.go
@@ -0,0 +1,110 @@
+//go:build windows
+// +build windows
+
+package checkups
+
+import (
+	"archive/zip"
+	"bytes"
+	"encoding/json"
+	"fmt"
+	"strings"
+	"time"
+
+	"github.com/kolide/launcher/pkg/launcher"
+	"golang.org/x/sys/windows/registry"
+)
+
+const (
+	installerInfoRegistryKeyFmt = `Software\Kolide\Launcher\%s\%s`
+	currentVersionKeyName       = `CurrentVersionNum`
+	installedVersionKeyName     = `InstalledVersionNum`
+	downloadPathKeyName         = `DownloadPath`
+	identifierKeyName           = `Identifier`
+	userKeyName                 = `User`
+	versionKeyName              = `Version`
+)
+
+type installerInfo struct {
+	// CurrentVersionNum is the numeric representation of our semver version, added at startup
+	CurrentVersionNum uint64 `json:"current_version_num"`
+	// InstalledVersionNum is the numeric representation of our semver version, added at install time
+	InstalledVersionNum uint64 `json:"installed_version_num"`
+	// Version is our semver string version representation, added at install time
+	Version string `json:"installed_version"`
+	// DownloadPath is the original location of the MSI used to install launcher
+	DownloadPath string `json:"download_path"`
+	Identifier   string `json:"identifier"`
+	User         string `json:"user"`
+}
+
+func gatherInstallerInfo(z *zip.Writer, identifier string) error {
+	if strings.TrimSpace(identifier) == "" {
+		identifier = launcher.DefaultLauncherIdentifier
+	}
+
+	info := installerInfo{
+		CurrentVersionNum: getDefaultRegistryIntValue(
+			fmt.Sprintf(installerInfoRegistryKeyFmt, identifier, currentVersionKeyName),
+		),
+		InstalledVersionNum: getDefaultRegistryIntValue(
+			fmt.Sprintf(installerInfoRegistryKeyFmt, identifier, installedVersionKeyName),
+		),
+		Version: getDefaultRegistryStringValue(
+			fmt.Sprintf(installerInfoRegistryKeyFmt, identifier, versionKeyName),
+		),
+		DownloadPath: getDefaultRegistryStringValue(
+			fmt.Sprintf(installerInfoRegistryKeyFmt, identifier, downloadPathKeyName),
+		),
+		Identifier: getDefaultRegistryStringValue(
+			fmt.Sprintf(installerInfoRegistryKeyFmt, identifier, identifierKeyName),
+		),
+		User: getDefaultRegistryStringValue(
+			fmt.Sprintf(installerInfoRegistryKeyFmt, identifier, userKeyName),
+		),
+	}
+
+	infoJson, err := json.MarshalIndent(info, "", "    ")
+	if err != nil {
+		return err
+	}
+
+	return addStreamToZip(z, "installer-info.json", time.Now(), bytes.NewReader(infoJson))
+}
+
+// getDefaultRegistryStringValue queries for the default registry value set at the provided path
+// on the local machine. this is a best effort approach, grabbing whatever info we can. not all
+// devices will have all paths/values present, errors are ignored
+func getDefaultRegistryStringValue(path string) string {
+	key, err := registry.OpenKey(registry.LOCAL_MACHINE, path, registry.QUERY_VALUE)
+	if err != nil {
+		return ""
+	}
+
+	defer key.Close()
+
+	val, _, err := key.GetStringValue("")
+	if err != nil {
+		return ""
+	}
+
+	return val
+}
+
+// getDefaultRegistryIntValue performs the same function as getDefaultRegistryStringValue but
+// is intended for integer (REG_DWORD) values
+func getDefaultRegistryIntValue(path string) uint64 {
+	key, err := registry.OpenKey(registry.LOCAL_MACHINE, path, registry.QUERY_VALUE)
+	if err != nil {
+		return 0
+	}
+
+	defer key.Close()
+
+	val, _, err := key.GetIntegerValue("")
+	if err != nil {
+		return 0
+	}
+
+	return val
+}
diff --git a/ee/debug/checkups/power_windows.go b/ee/debug/checkups/power_windows.go
index 6fd2eda86..6c988ed4f 100644
--- a/ee/debug/checkups/power_windows.go
+++ b/ee/debug/checkups/power_windows.go
@@ -54,12 +54,12 @@ func (p *powerCheckup) Run(ctx context.Context, extraWriter io.Writer) error {
 	hideWindow(powerCfgSleepStatesCmd)
 	availableSleepStatesOutput, err := powerCfgSleepStatesCmd.CombinedOutput()
 	if err != nil {
-		return fmt.Errorf("running powercfg.exe for sleep states: error %w", err)
+		return fmt.Errorf("running powercfg.exe for sleep states: error %w, output %s", err, string(availableSleepStatesOutput))
 	}
 
 	// Add sleep states using addStreamToZip
 	if err := addStreamToZip(extraZip, "available_sleep_states.txt", time.Now(), bytes.NewReader(availableSleepStatesOutput)); err != nil {
-		return fmt.Errorf("running powercfg.exe for sleep states: error %w, output %s", err, string(availableSleepStatesOutput))
+		return fmt.Errorf("adding sleep states stream to zip: %w", err)
 	}
 
 	// Get power events