diff --git a/ee/debug/checkups/checkups.go b/ee/debug/checkups/checkups.go
index 199ecee87..42ef6801d 100644
--- a/ee/debug/checkups/checkups.go
+++ b/ee/debug/checkups/checkups.go
@@ -125,6 +125,7 @@ func checkupsFor(k types.Knapsack, target targetBits) []checkupInt {
 		{&uninstallHistoryCheckup{k: k}, flareSupported},
 		{&desktopMenu{k: k}, flareSupported},
 		{&coredumpCheckup{}, doctorSupported | flareSupported},
+		{&downloadDirectory{}, flareSupported},
 	}
 
 	checkupsToRun := make([]checkupInt, 0)
diff --git a/ee/debug/checkups/download_directory.go b/ee/debug/checkups/download_directory.go
new file mode 100644
index 000000000..5079f9953
--- /dev/null
+++ b/ee/debug/checkups/download_directory.go
@@ -0,0 +1,120 @@
+package checkups
+
+import (
+	"context"
+	"fmt"
+	"io"
+	"os"
+	"path/filepath"
+	"runtime"
+	"strings"
+)
+
+type downloadDirectory struct {
+	status  Status
+	summary string
+	files   []fileInfo
+}
+
+func (c *downloadDirectory) Name() string {
+	return "Kolide Downloads"
+}
+
+func (c *downloadDirectory) Run(_ context.Context, extraFH io.Writer) error {
+	downloadDirs := getDownloadDirs()
+	if len(downloadDirs) == 0 {
+		c.status = Erroring
+		c.summary = "No download directories found"
+		return nil
+	}
+
+	for _, downloadDir := range downloadDirs {
+		pattern := filepath.Join(downloadDir, "kolide-launcher*")
+		matches, err := filepath.Glob(pattern)
+
+		if err != nil {
+			fmt.Fprintf(extraFH, "Error listing files in directory (%s): %s\n", downloadDir, err)
+			continue
+		}
+
+		for _, match := range matches {
+			if info, err := os.Stat(match); err == nil {
+				c.files = append(c.files, fileInfo{
+					Name:    match,
+					ModTime: info.ModTime(),
+				})
+			}
+		}
+	}
+
+	switch {
+	case len(c.files) == 0:
+		c.status = Informational
+		c.summary = "No Kolide installers found in any user's download directory"
+	default:
+		c.status = Informational
+		fileInfos := make([]string, len(c.files))
+		for i, file := range c.files {
+			fileName := filepath.Base(file.Name)
+			modTime := file.ModTime.Format("Mon, 02 Jan 2006 15:04:05 MST")
+			fileInfos[i] = fmt.Sprintf("%s (Modified: %s)", fileName, modTime)
+		}
+		installerList := strings.Join(fileInfos, ", ")
+		c.summary = fmt.Sprintf("Found Kolide installer(s) across user download directories: %s", installerList)
+	}
+
+	if len(c.files) > 0 {
+		fmt.Fprintln(extraFH, "Kolide installers found:")
+		for _, file := range c.files {
+			fmt.Fprintln(extraFH, file)
+		}
+	}
+
+	return nil
+}
+
+func (c *downloadDirectory) ExtraFileName() string {
+	return "kolide-installers-all-users.txt"
+}
+
+func (c *downloadDirectory) Status() Status {
+	return c.status
+}
+
+func (c *downloadDirectory) Summary() string {
+	return c.summary
+}
+
+func (c *downloadDirectory) Data() any {
+	return c.files
+}
+
+func getDownloadDirs() []string {
+	var userDirs []string
+	var baseDir string
+
+	if runtime.GOOS == "windows" {
+		baseDir = "C:\\Users"
+	} else if runtime.GOOS == "darwin" {
+		baseDir = "/Users"
+	} else {
+		baseDir = "/home"
+	}
+
+	entries, err := os.ReadDir(baseDir)
+	if err != nil {
+		return nil
+	}
+
+	for _, entry := range entries {
+		if !entry.IsDir() {
+			continue
+		}
+		userDir := filepath.Join(baseDir, entry.Name(), "Downloads")
+		if _, err := os.Stat(userDir); err == nil {
+			userDirs = append(userDirs, userDir)
+		}
+	}
+
+	return userDirs
+}