diff --git a/lib/client/https_client.go b/lib/client/https_client.go
index 11e263a6d519e..f382bb2354759 100644
--- a/lib/client/https_client.go
+++ b/lib/client/https_client.go
@@ -61,7 +61,7 @@ func httpTransport(insecure bool, pool *x509.CertPool) *http.Transport {
 
 func NewWebClient(url string, opts ...roundtrip.ClientParam) (*WebClient, error) {
 	opts = append(opts, roundtrip.SanitizerEnabled(true))
-	clt, err := roundtrip.NewClient(url, "", opts...)
+	clt, err := roundtrip.NewClient(url, "" /* version prefix */, opts...)
 	if err != nil {
 		return nil, trace.Wrap(err)
 	}
diff --git a/lib/httplib/httplib.go b/lib/httplib/httplib.go
index 8b241584817da..b354f16c8de03 100644
--- a/lib/httplib/httplib.go
+++ b/lib/httplib/httplib.go
@@ -212,14 +212,25 @@ func ConvertResponse(re *roundtrip.Response, err error) (*roundtrip.Response, er
 	return re, trace.ReadError(re.Code(), re.Bytes())
 }
 
+// Version describes the parts of a semver version
+// in the format: major.minor.patch-preRelease
 type Version struct {
-	Major      int64  `json:"major"`
-	Minor      int64  `json:"minor"`
-	Patch      int64  `json:"patch"`
-	String     string `json:"string"`
+	// Major is the first part of version.
+	Major int64 `json:"major"`
+	// Minor is the second part of version.
+	Minor int64 `json:"minor"`
+	// Patch is the third part of version.
+	Patch int64 `json:"patch"`
+	// PreRelease is only defined if there was a hyphen
+	// and a word at the end of version eg: the prerelease
+	// value of version 18.0.0-dev is "dev".
 	PreRelease string `json:"preRelease"`
+	// String contains the whole version.
+	String string `json:"string"`
 }
 
+// ReplyRouteNotFoundJSONWithVersionField writes a JSON error reply containing
+// a not found error, a Version object, and a not found HTTP status code.
 func ReplyRouteNotFoundJSONWithVersionField(w http.ResponseWriter, versionStr string) {
 	SetDefaultSecurityHeaders(w.Header())
 
diff --git a/lib/web/apiserver.go b/lib/web/apiserver.go
index 5fbc854daf549..588d9a5eec4ac 100644
--- a/lib/web/apiserver.go
+++ b/lib/web/apiserver.go
@@ -614,6 +614,7 @@ func NewHandler(cfg Config, opts ...HandlerOption) (*APIHandler, error) {
 		h.nodeWatcher = cfg.NodeWatcher
 	}
 
+	v1Prefix := "/v1"
 	notFoundRoutingHandler := http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
 		// Request is going to the API?
 		// If no routes were matched, it could be because it's a path with `v1` prefix
@@ -624,14 +625,18 @@ func NewHandler(cfg Config, opts ...HandlerOption) (*APIHandler, error) {
 		// and should be kept that way to prevent breakage.
 		//
 		// v2+ prefixes will be expected by both caller and definition and will not be stripped.
-		if matches := apiPrefixRegex.FindStringSubmatch(r.URL.Path); matches != nil && len(matches) == 3 {
-			postVersionPrefixPath := fmt.Sprintf("/%s", matches[2])
-			versionNum := matches[1]
-
-			// Regex check the rest of path to ensure we aren't allowing paths like /v1/v2/webapi
-			if matches := apiPrefixRegex.FindStringSubmatch(postVersionPrefixPath); matches == nil && versionNum == "1" {
-				http.StripPrefix("/v1", h).ServeHTTP(w, r)
-				return
+		if strings.HasPrefix(r.URL.Path, v1Prefix) {
+			pathParts := strings.Split(r.URL.Path, "/")
+			if len(pathParts) > 2 {
+				// check against known second part of path to ensure we
+				// aren't allowing paths like /v1/v2/webapi
+				// part[0] is empty space from leading slash "/"
+				// part[1] is the prefix "v1"
+				switch pathParts[2] {
+				case "webapi", "enterprise", "scripts", ".well-known", "workload-identity":
+					http.StripPrefix(v1Prefix, h).ServeHTTP(w, r)
+					return
+				}
 			}
 			httplib.ReplyRouteNotFoundJSONWithVersionField(w, teleport.Version)
 			return
diff --git a/lib/web/apiserver_test.go b/lib/web/apiserver_test.go
index e1f1e87e4fcfe..df3a53159c741 100644
--- a/lib/web/apiserver_test.go
+++ b/lib/web/apiserver_test.go
@@ -3491,7 +3491,7 @@ func TestEndpointNotFoundHandling(t *testing.T) {
 		},
 		{
 			name:      "invalid just prefix",
-			endpoint:  "v1/",
+			endpoint:  "v1",
 			shouldErr: true,
 		},
 		{