diff --git a/pkg/launcher/paths.go b/pkg/launcher/paths.go
index 8592c54cd..46b8a3229 100644
--- a/pkg/launcher/paths.go
+++ b/pkg/launcher/paths.go
@@ -39,7 +39,7 @@ func DefaultPath(path defaultPath) string {
 	if runtime.GOOS == "windows" {
 		switch path {
 		case RootDirectory:
-			return "C:\\Program Files\\Kolide\\Launcher-kolide-k2\\data"
+			return "C:\\ProgramData\\Kolide\\Launcher-kolide-k2\\data"
 		case WindowsConfigDirectory:
 			return "C:\\Program Files\\Kolide\\Launcher-kolide-k2\\conf"
 		case BinDirectory:
diff --git a/pkg/packagekit/assets/main.wxs b/pkg/packagekit/assets/main.wxs
index b9f376bbd..1238c979e 100644
--- a/pkg/packagekit/assets/main.wxs
+++ b/pkg/packagekit/assets/main.wxs
@@ -70,6 +70,7 @@
 	Level="1"
 	Display="hidden">
       <ComponentGroupRef Id="AppFiles" />
+      <ComponentGroupRef Id="AppData" />
     </Feature>
 
     <Feature
diff --git a/pkg/packagekit/package_wix.go b/pkg/packagekit/package_wix.go
index 8531a2351..4e8a8204a 100644
--- a/pkg/packagekit/package_wix.go
+++ b/pkg/packagekit/package_wix.go
@@ -137,7 +137,7 @@ func PackageWixMSI(ctx context.Context, w io.Writer, po *PackageOptions, include
 		wixArgs = append(wixArgs, wix.WithService(launcherService))
 	}
 
-	wixTool, err := wix.New(po.Root, mainWxsContent.Bytes(), wixArgs...)
+	wixTool, err := wix.New(po.Root, po.Identifier, mainWxsContent.Bytes(), wixArgs...)
 	if err != nil {
 		return fmt.Errorf("making wixTool: %w", err)
 	}
diff --git a/pkg/packagekit/wix/wix.go b/pkg/packagekit/wix/wix.go
index 9c7c41343..1941714ed 100644
--- a/pkg/packagekit/wix/wix.go
+++ b/pkg/packagekit/wix/wix.go
@@ -11,21 +11,24 @@ import (
 	"strings"
 
 	"github.com/go-kit/kit/log/level"
+	"github.com/kolide/kit/fsutil"
 	"github.com/kolide/launcher/pkg/contexts/ctxlog"
 )
 
 type wixTool struct {
-	wixPath        string     // Where is wix installed
-	packageRoot    string     // What's the root of the packaging files?
-	buildDir       string     // The wix tools want to work in a build dir.
-	msArch         string     // What's the Microsoft architecture name?
-	services       []*Service // array of services.
-	dockerImage    string     // If in docker, what image?
-	skipValidation bool       // Skip light validation. Seems to be needed for running in 32bit wine environments.
-	skipCleanup    bool       // Skip cleaning temp dirs. Useful when debugging wix generation
-	cleanDirs      []string   // directories to rm on cleanup
-	ui             bool       // whether or not to include a ui
-	extraFiles     []extraFile
+	wixPath         string     // Where is wix installed
+	packageRoot     string     // What's the root of the packaging files?
+	packageDataRoot string     // What's the root for the data directory packaging files?
+	buildDir        string     // The wix tools want to work in a build dir.
+	msArch          string     // What's the Microsoft architecture name?
+	services        []*Service // array of services.
+	dockerImage     string     // If in docker, what image?
+	skipValidation  bool       // Skip light validation. Seems to be needed for running in 32bit wine environments.
+	skipCleanup     bool       // Skip cleaning temp dirs. Useful when debugging wix generation
+	cleanDirs       []string   // directories to rm on cleanup
+	ui              bool       // whether or not to include a ui
+	extraFiles      []extraFile
+	identifier      string // the package identifier used for directory path creation (e.g. kolide-k2)
 
 	execCC func(context.Context, string, ...string) *exec.Cmd // Allows test overrides
 }
@@ -102,12 +105,12 @@ func SkipCleanup() WixOpt {
 // New takes a packageRoot of files, and a wxsContent of xml wix
 // configuration, and will return a struct with methods for building
 // packages with.
-func New(packageRoot string, mainWxsContent []byte, wixOpts ...WixOpt) (*wixTool, error) {
+func New(packageRoot string, identifier string, mainWxsContent []byte, wixOpts ...WixOpt) (*wixTool, error) {
 	wo := &wixTool{
 		wixPath:     FindWixInstall(),
 		packageRoot: packageRoot,
-
-		execCC: exec.CommandContext, //nolint:forbidigo // Fine to use exec.CommandContext outside of launcher proper
+		identifier:  identifier,
+		execCC:      exec.CommandContext, //nolint:forbidigo // Fine to use exec.CommandContext outside of launcher proper
 	}
 
 	for _, opt := range wixOpts {
@@ -169,6 +172,10 @@ func (wo *wixTool) Cleanup() {
 // Package will run through the wix steps to produce a resulting
 // package. The path for the resultant package will be returned.
 func (wo *wixTool) Package(ctx context.Context) (string, error) {
+	if err := wo.setupDataDir(ctx); err != nil {
+		return "", fmt.Errorf("adding data file stubs: %w", err)
+	}
+
 	if err := wo.heat(ctx); err != nil {
 		return "", fmt.Errorf("running heat: %w", err)
 	}
@@ -236,6 +243,57 @@ func (wo *wixTool) addServices(ctx context.Context) error {
 	return nil
 }
 
+// setupDataDir handles the windows data directory setup by pre-creating any files
+// that we want to ensure are cleaned up on uninstall.
+// this is handled before the other heat/candle/light calls because we must issue
+// a separate heat call to harvest the data directory in ProgramData instead of Program Files
+func (wo *wixTool) setupDataDir(ctx context.Context) error {
+	var err error
+	wo.packageDataRoot, err = os.MkdirTemp("", "package.packageDataRoot")
+	if err != nil {
+		return fmt.Errorf("unable to create temporary packaging data directory: %w", err)
+	}
+
+	wo.cleanDirs = append(wo.cleanDirs, wo.packageDataRoot)
+
+	fullIdentifier := fmt.Sprintf("Launcher-%s", wo.identifier)
+	dataFilesPath := filepath.Join(wo.packageDataRoot, fullIdentifier, "data")
+
+	if err := os.MkdirAll(dataFilesPath, fsutil.DirMode); err != nil {
+		return fmt.Errorf("create base data dir error for wix harvest: %w", err)
+	}
+
+	// touch these known file names before harvest to ensure they're cleaned up on uninstall
+	dataFilenames := []string{"launcher.db", "metadata.json", "kv.sqlite"}
+
+	for _, fname := range dataFilenames {
+		newPath := filepath.Join(dataFilesPath, fname)
+		newFile, err := os.Create(newPath)
+		if err != nil {
+			return err
+		}
+
+		newFile.Close()
+	}
+
+	_, err = wo.execOut(ctx,
+		filepath.Join(wo.wixPath, "heat.exe"),
+		"dir", wo.packageDataRoot,
+		"-nologo",
+		"-gg", "-g1",
+		"-srd",
+		"-sfrag",
+		"-ke",
+		"-cg", "AppData",
+		"-template", "fragment",
+		"-dr", "DATADIR",
+		"-var", "var.SourceDataDir",
+		"-out", "AppData.wxs",
+	)
+
+	return err
+}
+
 // heat invokes wix's heat command. This examines a directory and
 // "harvests" the files into an xml structure. See
 // http://wixtoolset.org/documentation/manual/v3/overview/heat.html
@@ -259,6 +317,7 @@ func (wo *wixTool) heat(ctx context.Context) error {
 		"-var", "var.SourceDir",
 		"-out", "AppFiles.wxs",
 	)
+
 	return err
 }
 
@@ -271,9 +330,11 @@ func (wo *wixTool) candle(ctx context.Context) error {
 		"-nologo",
 		"-arch", wo.msArch,
 		"-dSourceDir="+wo.packageRoot,
+		"-dSourceDataDir="+wo.packageDataRoot,
 		"-ext", "WixUtilExtension",
 		"Installer.wxs",
 		"AppFiles.wxs",
+		"AppData.wxs",
 	)
 	return err
 }
@@ -286,8 +347,10 @@ func (wo *wixTool) light(ctx context.Context) error {
 		"-nologo",
 		"-dcl:high", // compression level
 		"-dSourceDir=" + wo.packageRoot,
+		"-dSourceDataDir=" + wo.packageDataRoot,
 		"-ext", "WixUtilExtension",
 		"AppFiles.wixobj",
+		"AppData.wixobj",
 		"Installer.wixobj",
 		"-out", "out.msi",
 	}
@@ -315,6 +378,7 @@ func (wo *wixTool) execOut(ctx context.Context, argv0 string, args ...string) (s
 		"run",
 		"--entrypoint", "",
 		"-v", fmt.Sprintf("%s:%s", wo.packageRoot, wo.packageRoot),
+		"-v", fmt.Sprintf("%s:%s", wo.packageDataRoot, wo.packageDataRoot),
 		"-v", fmt.Sprintf("%s:%s", wo.buildDir, wo.buildDir),
 		"-w", wo.buildDir,
 		wo.dockerImage,
diff --git a/pkg/packagekit/wix/wix_test.go b/pkg/packagekit/wix/wix_test.go
index a0c86bab3..484448f9a 100644
--- a/pkg/packagekit/wix/wix_test.go
+++ b/pkg/packagekit/wix/wix_test.go
@@ -42,6 +42,7 @@ func TestWixPackage(t *testing.T) {
 	require.NoError(t, err)
 
 	wixTool, err := New(packageRoot,
+		"test-identifier",
 		mainWxsContent,
 		As32bit(),                 // wine is 32bit
 		SkipValidation(),          // wine can't validate
diff --git a/pkg/packaging/packaging.go b/pkg/packaging/packaging.go
index 1d6fc6510..8517af7d4 100644
--- a/pkg/packaging/packaging.go
+++ b/pkg/packaging/packaging.go
@@ -125,7 +125,7 @@ func (p *PackageOptions) Build(ctx context.Context, packageWriter io.Writer, tar
 
 	launcherMapFlags := map[string]string{
 		"hostname":           p.Hostname,
-		"root_directory":     p.canonicalizePath(p.rootDir),
+		"root_directory":     p.canonicalizeRootDir(p.rootDir),
 		"osqueryd_path":      p.canonicalizePath(filepath.Join(p.binDir, "osqueryd")),
 		"enroll_secret_path": p.canonicalizePath(filepath.Join(p.confDir, "secret")),
 	}
@@ -736,12 +736,19 @@ func (p *PackageOptions) setupDirectories() error {
 		// to take that into account for the guid generation.
 		p.binDir = filepath.Join("Launcher-"+p.Identifier, "bin")
 		p.confDir = filepath.Join("Launcher-"+p.Identifier, "conf")
+		// we handle the data directory setup differently for windows before final package generation,
+		// see wix/wix.go's setupDataDir method for additional context
 		p.rootDir = filepath.Join("Launcher-"+p.Identifier, "data")
 	default:
 		return fmt.Errorf("unknown platform %s", string(p.target.Platform))
 	}
 
 	for _, d := range []string{p.binDir, p.confDir, p.rootDir} {
+		// don't create the root (data) directory for windows before heat can run
+		if p.target.Platform == Windows && d == p.rootDir {
+			continue
+		}
+
 		if err := os.MkdirAll(filepath.Join(p.packageRoot, d), fsutil.DirMode); err != nil {
 			return fmt.Errorf("create dir (%s) for %s: %w", d, p.target.String(), err)
 		}
@@ -785,3 +792,15 @@ func (p *PackageOptions) canonicalizePath(path string) string {
 
 	return filepath.Join(`C:\Program Files\Kolide`, path)
 }
+
+// canonicalizeRootDir functions similarly to canonicalizePath above,
+// only impacting MSI targets. This is broken out from canonicalizePath
+// because for windows the full path to the root directory should be expanded
+// into ProgramData
+func (p *PackageOptions) canonicalizeRootDir(path string) string {
+	if p.target.Package != Msi {
+		return path
+	}
+
+	return filepath.Join(`C:\ProgramData\Kolide`, path)
+}