diff --git a/src/command/commands.c b/src/command/commands.c
index 6db8f5d3..53f06b95 100644
--- a/src/command/commands.c
+++ b/src/command/commands.c
@@ -651,12 +651,14 @@ cmd_account(ProfWin *window, const char *const command, gchar **args)
                     cons_show("");
                 } else if (strcmp(property, "pgpkeyid") == 0) {
 #ifdef HAVE_LIBGPGME
-                    if (!p_gpg_valid_key(value)) {
-                        cons_show("Invalid PGP key ID specified, see /pgp keys");
+                    char *err_str = NULL;
+                    if (!p_gpg_valid_key(value, &err_str)) {
+                        cons_show("Invalid PGP key ID specified: %s, see /pgp keys", err_str);
                     } else {
                         accounts_set_pgp_keyid(account_name, value);
                         cons_show("Updated PGP key ID for account %s: %s", account_name, value);
                     }
+                    free(err_str);
 #else
                     cons_show("PGP support is not included in this build.");
 #endif
@@ -5319,11 +5321,14 @@ cmd_pgp(ProfWin *window, const char *const command, gchar **args)
         }
 
         ProfAccount *account = accounts_get_account(jabber_get_account_name());
-        if (!p_gpg_valid_key(account->pgp_keyid)) {
-            ui_current_print_formatted_line('!', 0, "You must specify a valid PGP key ID for this account to start PGP encryption.");
+        char *err_str = NULL;
+        if (!p_gpg_valid_key(account->pgp_keyid, &err_str)) {
+            ui_current_print_formatted_line('!', 0, "Invalid PGP key ID %s: %s, cannot start PGP encryption.", account->pgp_keyid, err_str);
+            free(err_str);
             account_free(account);
             return TRUE;
         }
+        free(err_str);
         account_free(account);
 
         if (!p_gpg_available(chatwin->barejid)) {
diff --git a/src/event/server_events.c b/src/event/server_events.c
index 5b4bed05..555bd9f6 100644
--- a/src/event/server_events.c
+++ b/src/event/server_events.c
@@ -102,11 +102,21 @@ sv_ev_roster_received(void)
         ui_show_roster();
     }
 
-    char *account = jabber_get_account_name();
+    char *account_name = jabber_get_account_name();
+
+    // check pgp key valid if specified
+    ProfAccount *account = accounts_get_account(account_name);
+    if (account && account->pgp_keyid) {
+        char *err_str = NULL;
+        if (!p_gpg_valid_key(account->pgp_keyid, &err_str)) {
+            cons_show_error("Invalid PGP key ID specified: %s, %s", account->pgp_keyid, err_str);
+        }
+        free(err_str);
+    }
 
     // send initial presence
-    resource_presence_t conn_presence = accounts_get_login_presence(account);
-    char *last_activity_str = accounts_get_last_activity(account);
+    resource_presence_t conn_presence = accounts_get_login_presence(account_name);
+    char *last_activity_str = accounts_get_last_activity(account_name);
     if (last_activity_str) {
         GDateTime *nowdt = g_date_time_new_now_utc();
 
diff --git a/src/pgp/gpg.c b/src/pgp/gpg.c
index 7828c934..b40df96f 100644
--- a/src/pgp/gpg.c
+++ b/src/pgp/gpg.c
@@ -424,12 +424,13 @@ p_gpg_libver(void)
 }
 
 gboolean
-p_gpg_valid_key(const char *const keyid)
+p_gpg_valid_key(const char *const keyid, char **err_str)
 {
     gpgme_ctx_t ctx;
     gpgme_error_t error = gpgme_new(&ctx);
     if (error) {
         log_error("GPG: Failed to create gpgme context. %s %s", gpgme_strsource(error), gpgme_strerror(error));
+        *err_str = strdup(gpgme_strerror(error));
         return FALSE;
     }
 
@@ -438,18 +439,21 @@ p_gpg_valid_key(const char *const keyid)
 
     if (error || key == NULL) {
         log_error("GPG: Failed to get key. %s %s", gpgme_strsource(error), gpgme_strerror(error));
+        *err_str = strdup(gpgme_strerror(error));
         gpgme_release(ctx);
         return FALSE;
     }
 
-    if (key) {
+    if (key == NULL) {
+        *err_str = strdup("Unknown error");
         gpgme_release(ctx);
-        gpgme_key_unref(key);
-        return TRUE;
+        return FALSE;
     }
 
     gpgme_release(ctx);
-    return FALSE;
+    gpgme_key_unref(key);
+    return TRUE;
+
 }
 
 gboolean
diff --git a/src/pgp/gpg.h b/src/pgp/gpg.h
index f699e889..5149343f 100644
--- a/src/pgp/gpg.h
+++ b/src/pgp/gpg.h
@@ -59,7 +59,7 @@ GHashTable* p_gpg_list_keys(void);
 void p_gpg_free_keys(GHashTable *keys);
 gboolean p_gpg_addkey(const char *const jid, const char *const keyid);
 GHashTable* p_gpg_pubkeys(void);
-gboolean p_gpg_valid_key(const char *const keyid);
+gboolean p_gpg_valid_key(const char *const keyid, char **err_str);
 gboolean p_gpg_available(const char *const barejid);
 const char* p_gpg_libver(void);
 char* p_gpg_sign(const char *const str, const char *const fp);
diff --git a/tests/unittests/pgp/stub_gpg.c b/tests/unittests/pgp/stub_gpg.c
index b31dc34c..02ccb4c8 100644
--- a/tests/unittests/pgp/stub_gpg.c
+++ b/tests/unittests/pgp/stub_gpg.c
@@ -28,7 +28,7 @@ char* p_gpg_sign(const char * const str, const char * const fp)
     return NULL;
 }
 
-gboolean p_gpg_valid_key(const char * const keyid)
+gboolean p_gpg_valid_key(const char * const keyid, char **err_str)
 {
     return FALSE;
 }