diff --git a/doc/management-notes.txt b/doc/management-notes.txt
index 17645c1d..f685af28 100644
--- a/doc/management-notes.txt
+++ b/doc/management-notes.txt
@@ -816,6 +816,7 @@ actual private key. When the SSL protocol needs to perform a sign
 operation, the data to be signed will be sent to the management interface
 via a notification as follows:
 
+>PK_SIGN:[BASE64_DATA],[ALG] (if client announces support for management version > 2)
 >PK_SIGN:[BASE64_DATA] (if client announces support for management version > 1)
 >RSA_SIGN:[BASE64_DATA] (only older clients will be prompted like this)
 
@@ -823,7 +824,7 @@ The management interface client should then create an appropriate signature of
 the (decoded) BASE64_DATA using the private key and return the SSL signature as
 follows:
 
-pk-sig   (or rsa-sig)
+pk-sig (or rsa-sig)
 [BASE64_SIG_LINE]
 .
 .
@@ -833,6 +834,12 @@ END
 Base 64 encoded output of RSA_private_encrypt for RSA or ECDSA_sign()
 for EC using OpenSSL or mbedtls_pk_sign() using mbed TLS will provide a
 correct signature.
+The rsa-sig interfaces expects PKCS1 padded signatures for RSA keys
+(RSA_PKCS1_PADDING). EC signatures are always unpadded.
+
+The padding field is only present when pk-sig is used and
+currently the following values can be requested PCKS1 and NOPADDING for RSA
+certificates and NOPADDING for EC certificates.
 
 This capability is intended to allow the use of arbitrary cryptographic
 service providers with OpenVPN via the management interface.
@@ -840,6 +847,10 @@ service providers with OpenVPN via the management interface.
 New and updated clients are expected to use the version command to announce
 a version > 1 and handle '>PK_SIGN' prompt and respond with 'pk-sig'.
 
+The older rsa-sig and pk-sig interfaces hav no capability to indidicate the
+requested padding algorithm. When the 'nopadding' using version >= 2 is required.
+To support TLS 1.3 with OpenSSL 1.1.1 supporting unpadded signatures is required.
+
 COMMAND -- certificate (OpenVPN 2.4 or higher)
 ----------------------------------------------
 Provides support for external storage of the certificate. Requires the
diff --git a/doc/openvpn.8 b/doc/openvpn.8
index e80d4696..3cd5d944 100644
--- a/doc/openvpn.8
+++ b/doc/openvpn.8
@@ -2739,10 +2739,13 @@ Allow management interface to override
 directives (client\-only).
 .\"*********************************************************
 .TP
-.B \-\-management\-external\-key
+.B \-\-management\-external\-key [nopadding] [pkcs1]
 Allows usage for external private key file instead of
 .B \-\-key
-option (client\-only).
+option (client\-only). The optional parameters nopadding and
+pkcs1 signal support for different padding algorithms. See
+doc/mangement-notes.txt for a complete description of this
+feature.
 .\"*********************************************************
 .TP
 .B \-\-management\-external\-cert certificate\-hint
diff --git a/src/openvpn/manage.c b/src/openvpn/manage.c
index 8b633f20..62d4bc7b 100644
--- a/src/openvpn/manage.c
+++ b/src/openvpn/manage.c
@@ -3639,18 +3639,30 @@ management_query_multiline_flatten(struct management *man,
 
 char *
 /* returns allocated base64 signature */
-management_query_pk_sig(struct management *man,
-                         const char *b64_data)
+management_query_pk_sig(struct management *man, const char *b64_data,
+                        const char *padding)
 {
     const char *prompt = "PK_SIGN";
     const char *desc = "pk-sign";
+    struct buffer buf_data = alloc_buf(strlen(b64_data) + strlen(padding) + 20);
+
     if (man->connection.client_version <= 1)
     {
         prompt = "RSA_SIGN";
         desc = "rsa-sign";
     }
-    return management_query_multiline_flatten(man, b64_data, prompt, desc,
+
+    buf_write(&buf_data, b64_data, (int) strlen(b64_data));
+    if (man->connection.client_version > 2)
+    {
+        buf_write(&buf_data, ",", (int) strlen(","));
+        buf_write(&buf_data, padding, (int) strlen(padding));
+    }
+    char* ret = management_query_multiline_flatten(man,
+            (char *)buf_bptr(&buf_data), prompt, desc,
             &man->connection.ext_key_state, &man->connection.ext_key_input);
+    free_buf(&buf_data);
+    return ret;
 }
 
 char *
diff --git a/src/openvpn/manage.h b/src/openvpn/manage.h
index d24abe09..5c35a5ca 100644
--- a/src/openvpn/manage.h
+++ b/src/openvpn/manage.h
@@ -31,7 +31,7 @@
 #include "socket.h"
 #include "mroute.h"
 
-#define MANAGEMENT_VERSION                      2
+#define MANAGEMENT_VERSION                      3
 #define MANAGEMENT_N_PASSWORD_RETRIES           3
 #define MANAGEMENT_LOG_HISTORY_INITIAL_SIZE   100
 #define MANAGEMENT_ECHO_BUFFER_SIZE           100
@@ -341,12 +341,18 @@ struct management *management_init(void);
 #ifdef MANAGEMENT_PF
 #define MF_CLIENT_PF         (1<<7)
 #endif
-#define MF_UNIX_SOCK       (1<<8)
-#define MF_EXTERNAL_KEY    (1<<9)
-#define MF_UP_DOWN          (1<<10)
-#define MF_QUERY_REMOTE     (1<<11)
-#define MF_QUERY_PROXY      (1<<12)
-#define MF_EXTERNAL_CERT    (1<<13)
+#define MF_UNIX_SOCK                (1<<8)
+#define MF_EXTERNAL_KEY             (1<<9)
+#define MF_EXTERNAL_KEY_NOPADDING   (1<<10)
+#define MF_EXTERNAL_KEY_PKCS1PAD    (1<<11)
+#define MF_UP_DOWN                  (1<<12)
+#define MF_QUERY_REMOTE             (1<<13)
+#define MF_QUERY_PROXY              (1<<14)
+#define MF_EXTERNAL_CERT            (1<<15)
+
+#define MF_RSA_PKCS1_PADDING       1
+#define MF_RSA_NO_PADDING          2
+
 
 bool management_open(struct management *man,
                      const char *addr,
@@ -430,7 +436,11 @@ void management_learn_addr(struct management *management,
 
 #endif
 
-char *management_query_pk_sig(struct management *man, const char *b64_data);
+#define PKSIG_PKCS1     1
+#define PK
+
+char *management_query_pk_sig(struct management *man, const char *b64_data,
+                              const char* pading);
 
 char *management_query_cert(struct management *man, const char *cert_name);
 
diff --git a/src/openvpn/options.c b/src/openvpn/options.c
index 406669a3..229d6ce3 100644
--- a/src/openvpn/options.c
+++ b/src/openvpn/options.c
@@ -2141,6 +2141,22 @@ options_postprocess_verify_ce(const struct options *options, const struct connec
 
 #endif
 
+#if defined(ENABLE_CRYPTOAPI)
+    if (o->cryptoapi_cert && (tls_version_max() >= TLS_VER_1_3))
+    {
+        msg(M_ERR, "Cryptoapi support currently is incompatible "
+                   "with OpenSSL 1.1.1/TLS 1.3");
+    }
+#endif
+#if  defined(ENABLE_MANAGEMENT)
+    if ((options->management_flags & MF_EXTERNAL_KEY) &&
+        !(options->management_flags & (MF_EXTERNAL_KEY_NOPADDING))
+        )
+    {
+        msg(M_ERR, "management-external-key with OpenSSL 1.1.1 requires "
+                   "the nopadding argument/support");
+    }
+#endif
     /*
      * Windows-specific options.
      */
@@ -3068,7 +3084,6 @@ options_postprocess_mutate(struct options *o)
         options_postprocess_http_proxy_override(o);
     }
 #endif
-
 #if P2MP
     /*
      * Save certain parms before modifying options via --pull
@@ -5151,9 +5166,33 @@ add_option(struct options *options,
         options->management_write_peer_info_file = p[1];
     }
 #ifdef ENABLE_MANAGEMENT
-    else if (streq(p[0], "management-external-key") && !p[1])
+    else if (streq(p[0], "management-external-key"))
     {
         VERIFY_PERMISSION(OPT_P_GENERAL);
+        for (int j = 1; j < MAX_PARMS && p[j] != NULL; ++j)
+        {
+            if (streq(p[j], "nopadding"))
+            {
+                options->management_flags |= MF_EXTERNAL_KEY_NOPADDING;
+            }
+            else if (p[1] && streq(p[1], "pkcs1"))
+            {
+                options->management_flags |= MF_EXTERNAL_KEY_PKCS1PAD;
+            }
+            else
+            {
+                msg(msglevel, "Unknown management-external-key flag: %s" , p[j]);
+            }
+        }
+        /*
+         * When no option is present, assume that only PKCS1
+         * padding is supported
+         */
+        if (! (options->management_flags &
+            (MF_EXTERNAL_KEY_NOPADDING | MF_EXTERNAL_KEY_PKCS1PAD)))
+        {
+            options->management_flags |= MF_EXTERNAL_KEY_PKCS1PAD;
+        }
         options->management_flags |= MF_EXTERNAL_KEY;
     }
     else if (streq(p[0], "management-external-cert") && p[1] && !p[2])
@@ -8456,4 +8495,4 @@ add_option(struct options *options,
     }
 err:
     gc_free(&gc);
-}
\ No newline at end of file
+}
diff --git a/src/openvpn/ssl_mbedtls.c b/src/openvpn/ssl_mbedtls.c
index f7e8c2d0..09b1a8fa 100644
--- a/src/openvpn/ssl_mbedtls.c
+++ b/src/openvpn/ssl_mbedtls.c
@@ -626,7 +626,6 @@ tls_ctx_use_external_signing_func(struct tls_root_ctx *ctx,
 }
 
 #ifdef ENABLE_MANAGEMENT
-
 /** Query the management interface for a signature, see external_sign_func. */
 static bool
 management_sign_func(void *sign_ctx, const void *src, size_t src_len,
@@ -641,7 +640,11 @@ management_sign_func(void *sign_ctx, const void *src, size_t src_len,
         goto cleanup;
     }
 
-    if (!(dst_b64 = management_query_pk_sig(management, src_b64)))
+    /*
+     * We only use PKCS1 signatures at the moment in mbed TLS,
+     * there the signature parameter is hardcoded
+     */
+    if (!(dst_b64 = management_query_pk_sig(management, src_b64, "PKCS1")))
     {
         goto cleanup;
     }
diff --git a/src/openvpn/ssl_openssl.c b/src/openvpn/ssl_openssl.c
index c2c8fdc0..237c2b55 100644
--- a/src/openvpn/ssl_openssl.c
+++ b/src/openvpn/ssl_openssl.c
@@ -1079,24 +1079,46 @@ openvpn_extkey_rsa_finish(RSA *rsa)
     return 1;
 }
 
-/* Pass the input hash in 'dgst' to management and get the signature back.
+/*
+ * Convert OpenSSL's constant to the strings used in the management
+ * interface query
+ */
+const char*
+get_sig_padding_name(const int padding)
+{
+    switch(padding)
+    {
+        case RSA_PKCS1_PADDING:
+            return "PKCS1";
+        case RSA_NO_PADDING:
+            return "NOPADDING";
+        default:
+            return "UNKNOWN";
+    }
+}
+
+/*
+ * Pass the input hash in 'dgst' to management and get the signature back.
  * On input siglen contains the capacity of the buffer 'sig'.
  * On return signature is in sig.
+ * pkcs1 controls if pkcs1 padding is required
  * Return value is signature length or -1 on error.
  */
 static int
 get_sig_from_man(const unsigned char *dgst, unsigned int dgstlen,
-                 unsigned char *sig, unsigned int siglen)
+                 unsigned char *sig, unsigned int siglen,
+                 int padding)
 {
     char *in_b64 = NULL;
     char *out_b64 = NULL;
     int len = -1;
 
-    /* convert 'dgst' to base64 */
-    if (management
-        && openvpn_base64_encode(dgst, dgstlen, &in_b64) > 0)
+    int bencret = openvpn_base64_encode(dgst, dgstlen, &in_b64);
+
+    if (management && bencret > 0)
     {
-        out_b64 = management_query_pk_sig(management, in_b64);
+        out_b64 = management_query_pk_sig(management, in_b64,
+                                          get_sig_padding_name(padding));
     }
     if (out_b64)
     {
@@ -1110,18 +1132,19 @@ get_sig_from_man(const unsigned char *dgst, unsigned int dgstlen,
 
 /* sign arbitrary data */
 static int
-rsa_priv_enc(int flen, const unsigned char *from, unsigned char *to, RSA *rsa, int padding)
+rsa_priv_enc(int flen, const unsigned char *from, unsigned char *to, RSA *rsa,
+             int padding)
 {
     unsigned int len = RSA_size(rsa);
     int ret = -1;
 
-    if (padding != RSA_PKCS1_PADDING)
+    if (padding != RSA_PKCS1_PADDING && padding != RSA_NO_PADDING)
     {
         RSAerr(RSA_F_RSA_OSSL_PRIVATE_ENCRYPT, RSA_R_UNKNOWN_PADDING_TYPE);
         return -1;
     }
 
-    ret = get_sig_from_man(from, flen, to, len);
+    ret = get_sig_from_man(from, flen, to, len, padding);
 
     return (ret == len)? ret : -1;
 }
@@ -1215,7 +1238,13 @@ ecdsa_sign(int type, const unsigned char *dgst, int dgstlen, unsigned char *sig,
            unsigned int *siglen, const BIGNUM *kinv, const BIGNUM *r, EC_KEY *ec)
 {
     int capacity = ECDSA_size(ec);
-    int len = get_sig_from_man(dgst, dgstlen, sig, capacity);
+    /*
+     * ECDSA does not seem to have proper constants for paddings since
+     * there are only signatures without padding at the moment, reuse
+     * RSA_NO_PADDING for now as it will trigger querying for "NOPADDING" in the
+     * management interface
+     */
+    int len = get_sig_from_man(dgst, dgstlen, sig, capacity, RSA_NO_PADDING);
 
     if (len > 0)
     {
