diff --git a/agent/PSProxy.Agent/PSProxy.Agent.cs b/agent/PSProxy.Agent/PSProxy.Agent.cs
index 6cb7091..c209a1a 100644
--- a/agent/PSProxy.Agent/PSProxy.Agent.cs
+++ b/agent/PSProxy.Agent/PSProxy.Agent.cs
@@ -95,6 +95,9 @@ namespace PSProxy.Agent
             using (var rsa = new RSACryptoServiceProvider())
             {
                 rsa.ImportParameters(ParseRsaPublicKey(pubDer));
+                // .NET Framework RSACryptoServiceProvider supports OAEP only as
+                // SHA-1 with the default empty OAEP label. The server accepts
+                // this format for PowerShell 5.1 agent compatibility.
                 encSecret = rsa.Encrypt(secret, true);
             }
             string hello = "HELLO " + B64Url(encSecret) + " " + B64Url(nonce) + "\n";
diff --git a/cmd/psproxy-server/main.go b/cmd/psproxy-server/main.go
index 79ef21e..c81c154 100644
--- a/cmd/psproxy-server/main.go
+++ b/cmd/psproxy-server/main.go
@@ -5,6 +5,7 @@ import (
 	"crypto/hmac"
 	"crypto/rand"
 	"crypto/rsa"
+	"crypto/sha1"
 	"crypto/sha256"
 	"crypto/tls"
 	"crypto/x509"
@@ -693,6 +694,25 @@ func handleAgent(conn net.Conn, br *bufio.Reader, server *TunnelServer) {
 	server.ClearSession(a)
 }
 
+func decryptSessionSecret(key *rsa.PrivateKey, encSecret []byte) ([]byte, error) {
+	label := []byte("PS-Proxy PSP1 session")
+	secret, err := rsa.DecryptOAEP(sha256.New(), rand.Reader, key, encSecret, label)
+	if err == nil {
+		return secret, nil
+	}
+
+	// RSACryptoServiceProvider.Encrypt(..., true), used by the .NET Framework
+	// PowerShell agent, means OAEP-SHA1 with the default empty OAEP label. Keep
+	// accepting that wire format so already-staged agents can enroll.
+	for _, legacyLabel := range [][]byte{nil, label} {
+		legacySecret, legacyErr := rsa.DecryptOAEP(sha1.New(), rand.Reader, key, encSecret, legacyLabel)
+		if legacyErr == nil {
+			return legacySecret, nil
+		}
+	}
+	return nil, err
+}
+
 func serverHandshake(conn net.Conn, br *bufio.Reader, key *rsa.PrivateKey) (*protocol.SecureCodec, error) {
 	line, err := br.ReadString('\n')
 	if err != nil {
@@ -713,7 +733,7 @@ func serverHandshake(conn net.Conn, br *bufio.Reader, key *rsa.PrivateKey) (*pro
 	if len(clientNonce) != 32 {
 		return nil, errors.New("invalid client nonce")
 	}
-	secret, err := rsa.DecryptOAEP(sha256.New(), rand.Reader, key, encSecret, []byte("PS-Proxy PSP1 session"))
+	secret, err := decryptSessionSecret(key, encSecret)
 	if err != nil {
 		return nil, err
 	}
diff --git a/cmd/psproxy-server/main_test.go b/cmd/psproxy-server/main_test.go
index f03a38c..fee9c52 100644
--- a/cmd/psproxy-server/main_test.go
+++ b/cmd/psproxy-server/main_test.go
@@ -5,6 +5,7 @@ import (
 	"crypto/hmac"
 	"crypto/rand"
 	"crypto/rsa"
+	"crypto/sha1"
 	"crypto/sha256"
 	"crypto/x509"
 	"encoding/base64"
@@ -131,6 +132,25 @@ func TestSingleListenerAcceptReturnsEOFAfterFirstConn(t *testing.T) {
 		t.Fatal("second accept should return EOF")
 	}
 }
+func TestDecryptSessionSecretAcceptsAgentSHA1OAEP(t *testing.T) {
+	key, err := rsa.GenerateKey(rand.Reader, 3072)
+	if err != nil {
+		t.Fatal(err)
+	}
+	secret := []byte("0123456789abcdef0123456789abcdef")
+	enc, err := rsa.EncryptOAEP(sha1.New(), rand.Reader, &key.PublicKey, secret, nil)
+	if err != nil {
+		t.Fatal(err)
+	}
+	got, err := decryptSessionSecret(key, enc)
+	if err != nil {
+		t.Fatal(err)
+	}
+	if string(got) != string(secret) {
+		t.Fatalf("got %q want %q", got, secret)
+	}
+}
+
 func TestServerSecureHandshakeEncryptedFrame(t *testing.T) {
 	key, err := rsa.GenerateKey(rand.Reader, 3072)
 	if err != nil {