diff --git a/src/command/command.c b/src/command/command.c
index 23d5bae4..82e53c05 100644
--- a/src/command/command.c
+++ b/src/command/command.c
@@ -594,9 +594,9 @@ static struct cmd_t command_defs[] =
 
     { "/otr",
         cmd_otr, parse_args, 1, 2, NULL,
-        { "/otr gen|myfp|theirfp|start|end|trust|untrust|log|warn|libver", "Off The Record encryption commands.",
-        { "/otr gen|myfp|theirfp|start|end|trust|untrust|log|warn|libver",
-          "-------------------------------------------------------------",
+        { "/otr gen|myfp|theirfp|start|end|trust|untrust|log|warn|libver|policy", "Off The Record encryption commands.",
+        { "/otr gen|myfp|theirfp|start|end|trust|untrust|log|warn|libver|policy",
+          "--------------------------------------------------------------------",
           "gen - Generate your private key.",
           "myfp - Show your fingerprint.",
           "theirfp - Show contacts fingerprint.",
@@ -607,6 +607,7 @@ static struct cmd_t command_defs[] =
           "log - How to log OTR messages, options are 'on', 'off' and 'redact', with redaction being the default.",
           "warn - Show when unencrypted messaging is being used in the title bar, options are 'on' and 'off' with 'on' being the default.",
           "libver - Show which version of the libotr library is being used.",
+          "policy - manual, opportunistic or always.",
           NULL } } },
 
     { "/outtype",
@@ -1327,6 +1328,10 @@ cmd_execute_default(const char * const inp)
                 ui_current_print_line("You are not currently connected.");
             } else {
 #ifdef HAVE_LIBOTR
+                if ((strcmp(prefs_get_string(PREF_OTR_POLICY), "always") == 0) && !otr_is_secure(recipient)) {
+                    cons_show_error("Failed to send message. Please check OTR policy");
+                    return TRUE;
+                }
                 if (otr_is_secure(recipient)) {
                     char *encrypted = otr_encrypt_message(recipient, inp);
                     if (encrypted != NULL) {
diff --git a/src/command/commands.c b/src/command/commands.c
index 0a96d318..c0729630 100644
--- a/src/command/commands.c
+++ b/src/command/commands.c
@@ -24,6 +24,7 @@
 #include <stdlib.h>
 #include <errno.h>
 #include <glib.h>
+#include <libotr/proto.h>
 
 #include "chat_session.h"
 #include "command/commands.h"
@@ -967,7 +968,24 @@ cmd_msg(gchar **args, struct cmd_help_t help)
                     cons_show_error("Failed to encrypt and send message,");
                 }
             } else {
-                message_send(msg, usr_jid);
+                char *policy = prefs_get_string(PREF_OTR_POLICY);
+
+                if (strcmp(policy, "always") == 0) {
+                    cons_show_error("Failed to send message. Please check OTR policy");
+                    return TRUE;
+                } else if (strcmp(policy, "opportunistic") == 0) {
+                    char *otr_base_tag = OTRL_MESSAGE_TAG_BASE;
+                    char *otr_v2_tag = OTRL_MESSAGE_TAG_V2;
+                    int N = strlen(otr_base_tag) + strlen(otr_v2_tag) + strlen(msg) + 1;
+                    char *temp = (char *) malloc( (unsigned) N*sizeof(char *) );
+                    strcpy( temp , msg );
+                    strcat( temp , otr_base_tag);
+                    strcat( temp, otr_v2_tag);
+                    message_send(temp, usr_jid);
+                    free(temp);
+                } else {
+                    message_send(msg, usr_jid);
+                }
                 ui_outgoing_msg("me", usr_jid, msg);
 
                 if (((win_type == WIN_CHAT) || (win_type == WIN_CONSOLE)) && prefs_get_boolean(PREF_CHLOG)) {
@@ -2610,6 +2628,27 @@ cmd_otr(gchar **args, struct cmd_help_t help)
         char *version = otr_libotr_version();
         cons_show("Using libotr version %s", version);
         return TRUE;
+    } else if (strcmp(args[0], "policy") == 0) {
+        if (args[1] == NULL) {
+            char *policy = prefs_get_string(PREF_OTR_POLICY);
+            cons_show("OTR policy is now set to: %s", policy);
+            return TRUE;
+        }
+
+        char *choice = args[1];
+        if (g_strcmp0(choice, "manual") == 0) {
+            prefs_set_string(PREF_OTR_POLICY, "manual");
+            cons_show("OTR policy is now set to: manual");
+        } else if (g_strcmp0(choice, "opportunistic") == 0) {
+            prefs_set_string(PREF_OTR_POLICY, "opportunistic");
+            cons_show("OTR policy is now set to: opportunistic");
+        } else if (g_strcmp0(choice, "always") == 0) {
+            prefs_set_string(PREF_OTR_POLICY, "always");
+            cons_show("OTR policy is now set to: always");
+        } else {
+            cons_show("OTR policy can be set to: manual, opportunistic or always.");
+        }
+        return TRUE;
     }
 
     if (jabber_get_connection_status() != JABBER_CONNECTED) {
diff --git a/src/config/preferences.c b/src/config/preferences.c
index 9cc91cb6..2d6aee79 100644
--- a/src/config/preferences.c
+++ b/src/config/preferences.c
@@ -45,6 +45,7 @@
 #define PREF_GROUP_PRESENCE "presence"
 #define PREF_GROUP_CONNECTION "connection"
 #define PREF_GROUP_ALIAS "alias"
+#define PREF_GROUP_OTR_POLICY "policy"
 
 static gchar *prefs_loc;
 static GKeyFile *prefs;
@@ -396,6 +397,8 @@ _get_group(preference_t pref)
         case PREF_LOG_ROTATE:
         case PREF_LOG_SHARED:
             return PREF_GROUP_LOGGING;
+        case PREF_OTR_POLICY:
+            return PREF_GROUP_OTR_POLICY;
         case PREF_AUTOAWAY_CHECK:
         case PREF_AUTOAWAY_MODE:
         case PREF_AUTOAWAY_MESSAGE:
@@ -466,6 +469,8 @@ _get_key(preference_t pref)
             return "otr";
         case PREF_OTR_WARN:
             return "otr.warn";
+        case PREF_OTR_POLICY:
+            return "otr.policy";
         case PREF_LOG_ROTATE:
             return "rotate";
         case PREF_LOG_SHARED:
@@ -500,6 +505,8 @@ _get_default_string(preference_t pref)
             return "off";
         case PREF_OTR_LOG:
             return "redact";
+        case PREF_OTR_POLICY:
+            return "manual";
         case PREF_STATUSES_CONSOLE:
         case PREF_STATUSES_CHAT:
         case PREF_STATUSES_MUC:
@@ -507,4 +514,4 @@ _get_default_string(preference_t pref)
         default:
             return NULL;
     }
-}
+}
\ No newline at end of file
diff --git a/src/config/preferences.h b/src/config/preferences.h
index 310b9032..48748883 100644
--- a/src/config/preferences.h
+++ b/src/config/preferences.h
@@ -64,7 +64,8 @@ typedef enum {
     PREF_OTR_LOG,
     PREF_OTR_WARN,
     PREF_LOG_ROTATE,
-    PREF_LOG_SHARED
+    PREF_LOG_SHARED,
+    PREF_OTR_POLICY
 } preference_t;
 
 typedef struct prof_alias_t {
diff --git a/src/otr/otrlibv3.c b/src/otr/otrlibv3.c
index 633d07b8..d1495c9a 100644
--- a/src/otr/otrlibv3.c
+++ b/src/otr/otrlibv3.c
@@ -34,7 +34,7 @@ otrlib_policy(void)
 char *
 otrlib_start_query(void)
 {
-    return "?OTR?v2?";
+    return "?OTR?v2? This user has requested an Off-the-Record private conversation. However, you do not have a plugin to support that. See http://otr.cypherpunks.ca/ for more information.";
 }
 
 static int
diff --git a/src/otr/otrlibv4.c b/src/otr/otrlibv4.c
index 01afa868..c55d2972 100644
--- a/src/otr/otrlibv4.c
+++ b/src/otr/otrlibv4.c
@@ -35,7 +35,7 @@ otrlib_policy(void)
 char *
 otrlib_start_query(void)
 {
-    return "?OTR?v2?";
+    return "?OTR?v2? This user has requested an Off-the-Record private conversation. However, you do not have a plugin to support that. See http://otr.cypherpunks.ca/ for more information.";
 }
 
 static const char*
diff --git a/src/server_events.c b/src/server_events.c
index 79cc0e26..bd63de82 100644
--- a/src/server_events.c
+++ b/src/server_events.c
@@ -32,6 +32,7 @@
 
 #ifdef HAVE_LIBOTR
 #include "otr/otr.h"
+#include <libotr/proto.h>
 #endif
 
 #include "ui/ui.h"
@@ -206,7 +207,28 @@ handle_incoming_message(char *from, char *message, gboolean priv)
 #ifdef HAVE_LIBOTR
     gboolean was_decrypted = FALSE;
     char *newmessage;
-    if (!priv) {
+
+   if (!priv) {
+        //check for OTR whitespace (opportunistic or always)
+        char *policy = prefs_get_string(PREF_OTR_POLICY);
+        if (strcmp(policy, "opportunistic") == 0 || strcmp(policy, "always") == 0) {
+            char *whitespace_base = strstr(message,OTRL_MESSAGE_TAG_BASE);
+            if (whitespace_base) {
+                if (strstr(message, OTRL_MESSAGE_TAG_V2) || strstr(message, OTRL_MESSAGE_TAG_V1)) {
+                    // Remove whitespace pattern for proper display in UI
+                    // Handle both BASE+TAGV1/2(16+8) and BASE+TAGV1+TAGV2(16+8+8)
+                    int tag_length = 24;
+                    if (strstr(message, OTRL_MESSAGE_TAG_V2) && strstr(message, OTRL_MESSAGE_TAG_V1)) {
+                        tag_length = 32;
+                    }
+                    memmove(whitespace_base, whitespace_base+tag_length, tag_length);
+                    log_debug("<%s>", message);
+                    char *otr_query_message = otr_start_query();
+                    cons_show("OTR Whitespace pattern detected. Attempting to start OTR session...");
+                    message_send(otr_query_message, from);
+                }
+            }
+        }
         newmessage = otr_decrypt_message(from, message, &was_decrypted);
 
         // internal OTR message
diff --git a/src/xmpp/message.c b/src/xmpp/message.c
index 6da2b367..4fc71f63 100644
--- a/src/xmpp/message.c
+++ b/src/xmpp/message.c
@@ -522,4 +522,3 @@ message_init_module(void)
     message_send_inactive = _message_send_inactive;
     message_send_gone = _message_send_gone;
 }
-