diff --git a/tools/capver/main.go b/tools/capver/main.go
index 1e4512c1..2f564b9d 100644
--- a/tools/capver/main.go
+++ b/tools/capver/main.go
@@ -23,6 +23,7 @@ const (
 	releasesURL = "https://api.github.com/repos/tailscale/tailscale/releases"
 	rawFileURL  = "https://github.com/tailscale/tailscale/raw/refs/tags/%s/tailcfg/tailcfg.go"
 	outputFile  = "../../hscontrol/capver/capver_generated.go"
+	testFile    = "../../hscontrol/capver/capver_test_data.go"
 )
 
 type Release struct {
@@ -63,14 +64,12 @@ func getCapabilityVersions() (map[string]tailcfg.CapabilityVersion, error) {
 		rawURL := fmt.Sprintf(rawFileURL, version)
 		resp, err := http.Get(rawURL)
 		if err != nil {
-			log.Printf("Error fetching raw file for version %s: %v\n", version, err)
 			continue
 		}
 		defer resp.Body.Close()
 
 		body, err := io.ReadAll(resp.Body)
 		if err != nil {
-			log.Printf("Error reading raw file for version %s: %v\n", version, err)
 			continue
 		}
 
@@ -80,15 +79,49 @@ func getCapabilityVersions() (map[string]tailcfg.CapabilityVersion, error) {
 			capabilityVersionStr := matches[1]
 			capabilityVersion, _ := strconv.Atoi(capabilityVersionStr)
 			versions[version] = tailcfg.CapabilityVersion(capabilityVersion)
-		} else {
-			log.Printf("Version: %s, CurrentCapabilityVersion not found\n", version)
 		}
 	}
 
 	return versions, nil
 }
 
-func writeCapabilityVersionsToFile(versions map[string]tailcfg.CapabilityVersion) error {
+func calculateMinSupportedCapabilityVersion(versions map[string]tailcfg.CapabilityVersion) tailcfg.CapabilityVersion {
+	// Get unique major.minor versions
+	majorMinorToCapVer := make(map[string]tailcfg.CapabilityVersion)
+
+	for version, capVer := range versions {
+		// Remove 'v' prefix and split by '.'
+		cleanVersion := strings.TrimPrefix(version, "v")
+		parts := strings.Split(cleanVersion, ".")
+		if len(parts) >= 2 {
+			majorMinor := parts[0] + "." + parts[1]
+			// Keep the earliest (lowest) capver for each major.minor
+			if existing, exists := majorMinorToCapVer[majorMinor]; !exists || capVer < existing {
+				majorMinorToCapVer[majorMinor] = capVer
+			}
+		}
+	}
+
+	// Sort major.minor versions
+	majorMinors := xmaps.Keys(majorMinorToCapVer)
+	sort.Strings(majorMinors)
+
+	// Take the latest 10 versions
+	supportedCount := 10
+	if len(majorMinors) < supportedCount {
+		supportedCount = len(majorMinors)
+	}
+
+	if supportedCount == 0 {
+		return 90 // fallback
+	}
+
+	// The minimum supported version is the oldest of the latest 10
+	oldestSupportedMajorMinor := majorMinors[len(majorMinors)-supportedCount]
+	return majorMinorToCapVer[oldestSupportedMajorMinor]
+}
+
+func writeCapabilityVersionsToFile(versions map[string]tailcfg.CapabilityVersion, minSupportedCapVer tailcfg.CapabilityVersion) error {
 	// Generate the Go code as a string
 	var content strings.Builder
 	content.WriteString("package capver\n\n")
@@ -127,7 +160,12 @@ func writeCapabilityVersionsToFile(versions map[string]tailcfg.CapabilityVersion
 	for _, capVer := range capsSorted {
 		fmt.Fprintf(&content, "\t%d:\t\t\"%s\",\n", capVer, capVarToTailscaleVer[capVer])
 	}
-	content.WriteString("}\n")
+	content.WriteString("}\n\n")
+
+	// Add the MinSupportedCapabilityVersion constant
+	content.WriteString("// MinSupportedCapabilityVersion represents the minimum capability version\n")
+	content.WriteString("// supported by this Headscale instance (latest 10 minor versions)\n")
+	fmt.Fprintf(&content, "const MinSupportedCapabilityVersion tailcfg.CapabilityVersion = %d\n", minSupportedCapVer)
 
 	// Format the generated code
 	formatted, err := format.Source([]byte(content.String()))
@@ -144,6 +182,138 @@ func writeCapabilityVersionsToFile(versions map[string]tailcfg.CapabilityVersion
 	return nil
 }
 
+func writeTestDataFile(versions map[string]tailcfg.CapabilityVersion, minSupportedCapVer tailcfg.CapabilityVersion) error {
+	// Get unique major.minor versions for test generation
+	majorMinorToCapVer := make(map[string]tailcfg.CapabilityVersion)
+
+	for version, capVer := range versions {
+		cleanVersion := strings.TrimPrefix(version, "v")
+		parts := strings.Split(cleanVersion, ".")
+		if len(parts) >= 2 {
+			majorMinor := parts[0] + "." + parts[1]
+			if existing, exists := majorMinorToCapVer[majorMinor]; !exists || capVer < existing {
+				majorMinorToCapVer[majorMinor] = capVer
+			}
+		}
+	}
+
+	// Sort major.minor versions
+	majorMinors := xmaps.Keys(majorMinorToCapVer)
+	sort.Strings(majorMinors)
+
+	// Take latest 10
+	supportedCount := 10
+	if len(majorMinors) < supportedCount {
+		supportedCount = len(majorMinors)
+	}
+
+	latest10 := majorMinors[len(majorMinors)-supportedCount:]
+	latest3 := majorMinors[len(majorMinors)-3:]
+	latest2 := majorMinors[len(majorMinors)-2:]
+
+	// Generate test data file content
+	var content strings.Builder
+	content.WriteString("package capver\n\n")
+	content.WriteString("// Generated DO NOT EDIT\n\n")
+	content.WriteString("import \"tailscale.com/tailcfg\"\n\n")
+
+	// Generate complete test struct for TailscaleLatestMajorMinor
+	content.WriteString("var tailscaleLatestMajorMinorTests = []struct {\n")
+	content.WriteString("\tn        int\n")
+	content.WriteString("\tstripV   bool\n")
+	content.WriteString("\texpected []string\n")
+	content.WriteString("}{\n")
+
+	// Latest 3 with v prefix
+	content.WriteString("\t{3, false, []string{")
+	for i, version := range latest3 {
+		content.WriteString(fmt.Sprintf("\"v%s\"", version))
+		if i < len(latest3)-1 {
+			content.WriteString(", ")
+		}
+	}
+	content.WriteString("}},\n")
+
+	// Latest 2 without v prefix
+	content.WriteString("\t{2, true, []string{")
+	for i, version := range latest2 {
+		content.WriteString(fmt.Sprintf("\"%s\"", version))
+		if i < len(latest2)-1 {
+			content.WriteString(", ")
+		}
+	}
+	content.WriteString("}},\n")
+
+	// Latest 10 without v prefix (all supported)
+	content.WriteString("\t{10, true, []string{\n")
+	for _, version := range latest10 {
+		content.WriteString(fmt.Sprintf("\t\t\"%s\",\n", version))
+	}
+	content.WriteString("\t}},\n")
+
+	// Empty case
+	content.WriteString("\t{0, false, nil},\n")
+	content.WriteString("}\n\n")
+
+	// Build capVerToTailscaleVer for test data
+	capVerToTailscaleVer := make(map[tailcfg.CapabilityVersion]string)
+	sortedVersions := xmaps.Keys(versions)
+	sort.Strings(sortedVersions)
+	for _, v := range sortedVersions {
+		cap := versions[v]
+		if _, ok := capVerToTailscaleVer[cap]; !ok {
+			capVerToTailscaleVer[cap] = v
+		}
+	}
+
+	// Generate complete test struct for CapVerMinimumTailscaleVersion
+	content.WriteString("var capVerMinimumTailscaleVersionTests = []struct {\n")
+	content.WriteString("\tinput    tailcfg.CapabilityVersion\n")
+	content.WriteString("\texpected string\n")
+	content.WriteString("}{\n")
+
+	// Add minimum supported version
+	minVersionString := capVerToTailscaleVer[minSupportedCapVer]
+	content.WriteString(fmt.Sprintf("\t{%d, \"%s\"},\n", minSupportedCapVer, minVersionString))
+
+	// Add a few more test cases
+	capsSorted := xmaps.Keys(capVerToTailscaleVer)
+	sort.Slice(capsSorted, func(i, j int) bool {
+		return capsSorted[i] < capsSorted[j]
+	})
+
+	testCount := 0
+	for _, capVer := range capsSorted {
+		if testCount >= 4 { // Limit to a few test cases
+			break
+		}
+		if capVer != minSupportedCapVer { // Don't duplicate the min version test
+			version := capVerToTailscaleVer[capVer]
+			content.WriteString(fmt.Sprintf("\t{%d, \"%s\"},\n", capVer, version))
+			testCount++
+		}
+	}
+
+	// Edge cases
+	content.WriteString("\t{9001, \"\"}, // Test case for a version higher than any in the map\n")
+	content.WriteString("\t{60, \"\"},   // Test case for a version lower than any in the map\n")
+	content.WriteString("}\n")
+
+	// Format the generated code
+	formatted, err := format.Source([]byte(content.String()))
+	if err != nil {
+		return fmt.Errorf("error formatting test data Go code: %w", err)
+	}
+
+	// Write to file
+	err = os.WriteFile(testFile, formatted, 0644)
+	if err != nil {
+		return fmt.Errorf("error writing test data file: %w", err)
+	}
+
+	return nil
+}
+
 func main() {
 	versions, err := getCapabilityVersions()
 	if err != nil {
@@ -151,11 +321,20 @@ func main() {
 		return
 	}
 
-	err = writeCapabilityVersionsToFile(versions)
+	// Calculate the minimum supported capability version
+	minSupportedCapVer := calculateMinSupportedCapabilityVersion(versions)
+
+	err = writeCapabilityVersionsToFile(versions, minSupportedCapVer)
 	if err != nil {
 		log.Println("Error writing to file:", err)
 		return
 	}
 
+	err = writeTestDataFile(versions, minSupportedCapVer)
+	if err != nil {
+		log.Println("Error writing test data file:", err)
+		return
+	}
+
 	log.Println("Capability versions written to", outputFile)
 }