diff --git a/cmd/cloudflared/updater/workers_service.go b/cmd/cloudflared/updater/workers_service.go
index 9e41eabd..23a40968 100644
--- a/cmd/cloudflared/updater/workers_service.go
+++ b/cmd/cloudflared/updater/workers_service.go
@@ -5,8 +5,6 @@ import (
 	"errors"
 	"net/http"
 	"runtime"
-	"strconv"
-	"strings"
 )
 
 // Options are the update options supported by the
@@ -28,6 +26,7 @@ type VersionResponse struct {
 	Checksum     string `json:"checksum"`
 	IsCompressed bool   `json:"compressed"`
 	UserMessage  string `json:"userMessage"`
+	ShouldUpdate bool   `json:"shouldUpdate"`
 	Error        string `json:"error"`
 }
 
@@ -86,71 +85,10 @@ func (s *WorkersService) Check() (CheckResult, error) {
 		return nil, errors.New(v.Error)
 	}
 
-	var versionToUpdate = ""
-	if s.opts.IsForced || IsNewerVersion(s.currentVersion, v.Version) {
+	versionToUpdate := ""
+	if v.ShouldUpdate {
 		versionToUpdate = v.Version
 	}
 
 	return NewWorkersVersion(v.URL, versionToUpdate, v.Checksum, s.targetPath, v.UserMessage, v.IsCompressed), nil
 }
-
-// IsNewerVersion checks semantic versioning for the latest version
-// cloudflared tagging is more of a date than a semantic version,
-// but the same comparision logic still holds for major.minor.patch
-// e.g. 2020.8.2 is newer than 2020.8.1.
-func IsNewerVersion(current string, check string) bool {
-	if strings.Contains(strings.ToLower(current), "dev") {
-		return false // dev builds shouldn't update
-	}
-
-	cMajor, cMinor, cPatch, err := SemanticParts(current)
-	if err != nil {
-		return false
-	}
-
-	nMajor, nMinor, nPatch, err := SemanticParts(check)
-	if err != nil {
-		return false
-	}
-
-	if nMajor > cMajor {
-		return true
-	}
-
-	if nMajor == cMajor && nMinor > cMinor {
-		return true
-	}
-
-	if nMajor == cMajor && nMinor == cMinor && nPatch > cPatch {
-		return true
-	}
-	return false
-}
-
-// SemanticParts gets the major, minor, and patch version of a semantic version string
-// e.g. 3.1.2 would return 3, 1, 2, nil
-func SemanticParts(version string) (major int, minor int, patch int, err error) {
-	major = 0
-	minor = 0
-	patch = 0
-	parts := strings.Split(version, ".")
-	if len(parts) != 3 {
-		err = errors.New("invalid version")
-		return
-	}
-	major, err = strconv.Atoi(parts[0])
-	if err != nil {
-		return
-	}
-
-	minor, err = strconv.Atoi(parts[1])
-	if err != nil {
-		return
-	}
-
-	patch, err = strconv.Atoi(parts[2])
-	if err != nil {
-		return
-	}
-	return
-}
diff --git a/cmd/cloudflared/updater/workers_service_test.go b/cmd/cloudflared/updater/workers_service_test.go
index 0476aa4a..ccf95c89 100644
--- a/cmd/cloudflared/updater/workers_service_test.go
+++ b/cmd/cloudflared/updater/workers_service_test.go
@@ -6,6 +6,7 @@ import (
 	"compress/gzip"
 	"crypto/sha256"
 	"encoding/json"
+	"errors"
 	"fmt"
 	"io/ioutil"
 	"log"
@@ -13,6 +14,8 @@ import (
 	"net/http/httptest"
 	"os"
 	"runtime"
+	"strconv"
+	"strings"
 	"testing"
 
 	"github.com/stretchr/testify/require"
@@ -68,8 +71,11 @@ func updateHandler(w http.ResponseWriter, r *http.Request) {
 	if query.Get(ClientVersionName) == knownBuggyVersion {
 		userMessage = expectedUserMsg
 	}
+	shouldUpdate := requestedVersion != "" || IsNewerVersion(query.Get(ClientVersionName), version)
 
-	v := VersionResponse{URL: url, Version: version, Checksum: checksum, UserMessage: userMessage}
+	v := VersionResponse{
+		URL: url, Version: version, Checksum: checksum, UserMessage: userMessage, ShouldUpdate: shouldUpdate,
+	}
 	respondWithJSON(w, v, http.StatusOK)
 }
 
@@ -81,7 +87,7 @@ func gzipUpdateHandler(w http.ResponseWriter, r *http.Request) {
 	checksum := fmt.Sprintf("%x", h.Sum(nil))
 
 	url := fmt.Sprintf("http://%s/gzip-download.tgz", r.Host)
-	v := VersionResponse{URL: url, Version: version, Checksum: checksum}
+	v := VersionResponse{URL: url, Version: version, Checksum: checksum, ShouldUpdate: true}
 	respondWithJSON(w, v, http.StatusOK)
 }
 
@@ -122,6 +128,64 @@ func failureHandler(w http.ResponseWriter, r *http.Request) {
 	respondWithJSON(w, VersionResponse{Error: "unsupported os and architecture"}, http.StatusBadRequest)
 }
 
+func IsNewerVersion(current string, check string) bool {
+	if current == "" || check == "" {
+		return false
+	}
+	if strings.Contains(strings.ToLower(current), "dev") {
+		return false // dev builds shouldn't update
+	}
+
+	cMajor, cMinor, cPatch, err := SemanticParts(current)
+	if err != nil {
+		return false
+	}
+
+	nMajor, nMinor, nPatch, err := SemanticParts(check)
+	if err != nil {
+		return false
+	}
+
+	if nMajor > cMajor {
+		return true
+	}
+
+	if nMajor == cMajor && nMinor > cMinor {
+		return true
+	}
+
+	if nMajor == cMajor && nMinor == cMinor && nPatch > cPatch {
+		return true
+	}
+	return false
+}
+
+func SemanticParts(version string) (major int, minor int, patch int, err error) {
+	major = 0
+	minor = 0
+	patch = 0
+	parts := strings.Split(version, ".")
+	if len(parts) != 3 {
+		err = errors.New("invalid version")
+		return
+	}
+	major, err = strconv.Atoi(parts[0])
+	if err != nil {
+		return
+	}
+
+	minor, err = strconv.Atoi(parts[1])
+	if err != nil {
+		return
+	}
+
+	patch, err = strconv.Atoi(parts[2])
+	if err != nil {
+		return
+	}
+	return
+}
+
 func createServer() *httptest.Server {
 	mux := http.NewServeMux()
 	mux.HandleFunc("/updater", updateHandler)
@@ -285,15 +349,3 @@ func TestUpdateWhenRunningKnownBuggyVersion(t *testing.T) {
 	require.Equal(t, v.Version(), mostRecentVersion)
 	require.Equal(t, v.UserMessage(), expectedUserMsg)
 }
-
-func TestVersionParsing(t *testing.T) {
-	require.False(t, IsNewerVersion("2020.8.2", "2020.8.2"))
-	require.True(t, IsNewerVersion("2020.8.2", "2020.8.3"))
-	require.True(t, IsNewerVersion("2020.8.2", "2021.1.2"))
-	require.True(t, IsNewerVersion("2020.8.2", "2020.9.1"))
-	require.True(t, IsNewerVersion("2020.8.2", "2020.12.45"))
-	require.False(t, IsNewerVersion("2020.8.2", "2020.6.3"))
-	require.False(t, IsNewerVersion("DEV", "2020.8.5"))
-	require.False(t, IsNewerVersion("2020.8.2", "asdlkfjasdf"))
-	require.True(t, IsNewerVersion("3.0.1", "4.2.1"))
-}