diff --git a/lib/client/api.go b/lib/client/api.go
index 8f4b13c4bd101..ac3f5e9c2297a 100644
--- a/lib/client/api.go
+++ b/lib/client/api.go
@@ -4155,9 +4155,9 @@ func (tc *TeleportClient) Ping(ctx context.Context) (*webclient.PingResponse, er
 		return nil, trace.Wrap(err)
 	}
 
-	// If version checking was requested and the server advertises a minimum version.
-	if tc.CheckVersions && pr.MinClientVersion != "" {
-		if err := utils.CheckVersion(teleport.Version, pr.MinClientVersion); err != nil && trace.IsBadParameter(err) {
+	// Verify server->client and client->server compatibility.
+	if tc.CheckVersions {
+		if !utils.MeetsVersion(teleport.Version, pr.MinClientVersion) {
 			fmt.Fprintf(tc.Stderr, `
 			WARNING
 			Detected potentially incompatible client and server versions.
@@ -4166,6 +4166,18 @@ func (tc *TeleportClient) Ping(ctx context.Context) (*webclient.PingResponse, er
 			Future versions of tsh will fail when incompatible versions are detected.
 			`, pr.MinClientVersion, teleport.Version, pr.MinClientVersion)
 		}
+
+		// Recent `tsh mfa` changes require at least Teleport v15.
+		const minServerVersion = "15.0.0-aa" // "-aa" matches all development versions
+		if !utils.MeetsVersion(pr.ServerVersion, minServerVersion) {
+			fmt.Fprintf(tc.Stderr, `
+			WARNING
+			Detected incompatible client and server versions.
+			Minimum server version supported by tsh is %v but your server is using %v.
+			Please use a tsh version that matches your server.
+			You may use the --skip-version-check flag to bypass this check.
+			`, minServerVersion, pr.ServerVersion)
+		}
 	}
 
 	// Update tc with proxy and auth settings specified in Ping response.
diff --git a/lib/utils/utils_test.go b/lib/utils/utils_test.go
index a56e560cc1605..85982c6e15262 100644
--- a/lib/utils/utils_test.go
+++ b/lib/utils/utils_test.go
@@ -149,6 +149,7 @@ func TestVersions(t *testing.T) {
 	for _, testCase := range successTestCases {
 		t.Run(testCase.info, func(t *testing.T) {
 			require.NoError(t, CheckVersion(testCase.client, testCase.minClient))
+			assert.True(t, MeetsVersion(testCase.client, testCase.minClient), "MeetsVersion expected to succeed")
 		})
 	}
 
@@ -159,6 +160,7 @@ func TestVersions(t *testing.T) {
 	for _, testCase := range failTestCases {
 		t.Run(testCase.info, func(t *testing.T) {
 			fixtures.AssertBadParameter(t, CheckVersion(testCase.client, testCase.minClient))
+			assert.False(t, MeetsVersion(testCase.client, testCase.minClient), "MeetsVersion expected to fail")
 		})
 	}
 }
diff --git a/lib/utils/ver.go b/lib/utils/ver.go
index 42c8d8263c1d6..34f796853e23a 100644
--- a/lib/utils/ver.go
+++ b/lib/utils/ver.go
@@ -21,6 +21,18 @@ import (
 	"github.com/gravitational/trace"
 )
 
+// MeetsVersion returns true if gotVer is empty or at least minVer.
+func MeetsVersion(gotVer, minVer string) bool {
+	if gotVer == "" {
+		return true // Ignore empty versions.
+	}
+
+	err := CheckVersion(gotVer, minVer)
+
+	// Non BadParameter errors are semver parsing errors.
+	return !trace.IsBadParameter(err)
+}
+
 // CheckVersion compares a version with a minimum version supported.
 func CheckVersion(currentVersion, minVersion string) error {
 	currentSemver, minSemver, err := versionStringToSemver(currentVersion, minVersion)
diff --git a/lib/utils/ver_test.go b/lib/utils/ver_test.go
index 56fa2a288bdf2..a78c0e30b96cc 100644
--- a/lib/utils/ver_test.go
+++ b/lib/utils/ver_test.go
@@ -18,6 +18,21 @@ package utils
 
 import "testing"
 
+func TestMeetsVersion_emptyOrInvalid(t *testing.T) {
+	// See TestVersions for more comprehensive tests.
+
+	if !MeetsVersion("", "v1.2.3") {
+		t.Error("MeetsVersion with an empty gotVer should always succeed")
+	}
+
+	if !MeetsVersion("banana", "v1.2.3") {
+		t.Error("MeetsVersion with an invalid version should always succeed")
+	}
+	if !MeetsVersion("v1.2.3", "banana") {
+		t.Error("MeetsVersion with an invalid version should always succeed")
+	}
+}
+
 func TestMinVerWithoutPreRelease(t *testing.T) {
 	t.Parallel()