diff --git a/lib/auth/webauthn/register.go b/lib/auth/webauthn/register.go
index 2f16c26569221..2d253598bec31 100644
--- a/lib/auth/webauthn/register.go
+++ b/lib/auth/webauthn/register.go
@@ -144,11 +144,16 @@ func (f *RegistrationFlow) Begin(ctx context.Context, user string, passwordless
 		if dev.GetU2F() != nil {
 			continue
 		}
-		// Skip resident/non-resident keys depending on whether it's a passwordless
-		// registration.
-		// Letting users have both allows them to "swap" between key types in the
-		// same device.
-		if webDev := dev.GetWebauthn(); webDev != nil && webDev.ResidentKey != passwordless {
+
+		// Let authenticator "upgrades" from non-resident (MFA) to resident
+		// (passwordless) happen, but prevent "downgrades" from resident to
+		// non-resident.
+		//
+		// Modern passkey implementations will "disobey" our MFA registrations and
+		// actually create passkeys, silently replacing the old passkey with the new
+		// "MFA" key, which can make Teleport confused (for example, by letting the
+		// "MFA" key be deleted because Teleport thinks the passkey still exists).
+		if webDev := dev.GetWebauthn(); webDev != nil && !webDev.ResidentKey && passwordless {
 			continue
 		}
 
diff --git a/lib/auth/webauthn/register_test.go b/lib/auth/webauthn/register_test.go
index fd4292aab18a4..8086198f747d9 100644
--- a/lib/auth/webauthn/register_test.go
+++ b/lib/auth/webauthn/register_test.go
@@ -138,32 +138,32 @@ func TestRegistrationFlow_Begin_excludeList(t *testing.T) {
 	const user = "llama"
 	const rpID = "localhost"
 
-	dev1ID := []byte{1, 1, 1} // U2F
-	web1ID := []byte{1, 1, 2} // WebAuthn / MFA
-	rk1ID := []byte{1, 1, 3}  // WebAuthn / passwordless
-	dev1 := &types.MFADevice{
+	u2fID := []byte{1, 1, 1}     // U2F
+	mfaID := []byte{1, 1, 2}     // WebAuthn / MFA
+	passkeyID := []byte{1, 1, 3} // WebAuthn / passwordless
+	u2fDev := &types.MFADevice{
 		Device: &types.MFADevice_U2F{
 			U2F: &types.U2FDevice{
-				KeyHandle: dev1ID,
+				KeyHandle: u2fID,
 			},
 		},
 	}
-	web1 := &types.MFADevice{
+	mfaDev := &types.MFADevice{
 		Device: &types.MFADevice_Webauthn{
 			Webauthn: &types.WebauthnDevice{
-				CredentialId: web1ID,
+				CredentialId: mfaID,
 			},
 		},
 	}
-	rk1 := &types.MFADevice{
+	passkeyDev := &types.MFADevice{
 		Device: &types.MFADevice_Webauthn{
 			Webauthn: &types.WebauthnDevice{
-				CredentialId: rk1ID,
+				CredentialId: passkeyID,
 				ResidentKey:  true,
 			},
 		},
 	}
-	identity := newFakeIdentity(user, dev1, web1, rk1)
+	identity := newFakeIdentity(user, u2fDev, mfaDev, passkeyDev)
 
 	rf := wanlib.RegistrationFlow{
 		Webauthn: &types.Webauthn{
@@ -179,13 +179,18 @@ func TestRegistrationFlow_Begin_excludeList(t *testing.T) {
 		wantExcludeList [][]byte
 	}{
 		{
-			name:            "MFA",
-			wantExcludeList: [][]byte{web1ID}, // U2F and resident excluded
+			name: "MFA",
+			wantExcludeList: [][]byte{
+				mfaID,
+				passkeyID, // Prevents "downgrades"
+			},
 		},
 		{
-			name:            "passwordless",
-			passwordless:    true,
-			wantExcludeList: [][]byte{rk1ID}, // U2F and MFA excluded
+			name:         "passwordless",
+			passwordless: true,
+			wantExcludeList: [][]byte{
+				passkeyID,
+			},
 		},
 	}
 	for _, test := range tests {