Index: b/agent/agent.h
===================================================================
--- b/agent/agent.h
+++ b/agent/agent.h
@@ -415,7 +415,7 @@
                      membuf_t *outbuf, int *r_padding);
 
 /*-- genkey.c --*/
-int check_passphrase_constraints (ctrl_t ctrl, const char *pw, int silent);
+int check_passphrase_constraints (ctrl_t ctrl, const char *pw, int silent, char **failed_constraint);
 gpg_error_t agent_ask_new_passphrase (ctrl_t ctrl, const char *prompt,
                                       char **r_passphrase);
 int agent_genkey (ctrl_t ctrl, const char *cache_nonce,
Index: b/agent/call-pinentry.c
===================================================================
--- b/agent/call-pinentry.c
+++ b/agent/call-pinentry.c
@@ -675,7 +675,7 @@
       else
         {
           percent = estimate_passphrase_quality (pin);
-          if (check_passphrase_constraints (NULL, pin, 1))
+          if (check_passphrase_constraints (NULL, pin, 1, NULL))
             percent = -percent;
           snprintf (numbuf, sizeof numbuf, "%d", percent);
           rc = assuan_send_data (ctx, numbuf, strlen (numbuf));
Index: b/agent/command.c
===================================================================
--- b/agent/command.c
+++ b/agent/command.c
@@ -1530,7 +1530,11 @@
         {
           int i;
 
-          if (opt_check && check_passphrase_constraints (ctrl, response, 0))
+          if (opt_check &&
+              check_passphrase_constraints (ctrl, response, 0,
+                                            &repeat_errtext) /* Override use of repeat_errtext
+                                                                for errtext */
+              )
             {
               xfree (response);
               goto next_try;
Index: b/agent/genkey.c
===================================================================
--- b/agent/genkey.c
+++ b/agent/genkey.c
@@ -153,11 +153,9 @@
   gpg_error_t err;
 
   if (opt.enforce_passphrase_constraints)
-    {
-      err = agent_show_message (ctrl, desc, _("Enter new passphrase"));
-      if (!err)
-        err = gpg_error (GPG_ERR_CANCELED);
-    }
+    /* Passphrase constraints errors are shown
+     * as error messages in password prompt */
+    err = gpg_error (GPG_ERR_CANCELED);
   else
     err = agent_get_confirmation (ctrl, desc,
                                   anyway_btn, _("Enter new passphrase"), 0);
@@ -175,9 +173,10 @@
 /* Check whether the passphrase PW is suitable. Returns 0 if the
    passphrase is suitable and true if it is not and the user should be
    asked to provide a different one.  If SILENT is set, no message are
-   displayed.  */
+   displayed. If FAILED_CONSTRAINT is set and SILENT is not, the error
+   messages are returned */
 int
-check_passphrase_constraints (ctrl_t ctrl, const char *pw, int silent)
+check_passphrase_constraints (ctrl_t ctrl, const char *pw, int silent, char **failed_constraint)
 {
   gpg_error_t err = 0;
   unsigned int minlen = opt.min_passphrase_len;
@@ -205,6 +204,9 @@
 
       err = take_this_one_anyway2 (ctrl, desc,
                                    _("Yes, protection is not needed"));
+      if (failed_constraint)
+        *failed_constraint = xstrdup (desc);
+
       goto leave;
     }
 
@@ -297,6 +299,8 @@
 
       /* Show error messages.  */
       err = take_this_one_anyway (ctrl, msg);
+      if (failed_constraint)
+        *failed_constraint = xtrystrdup (msg);
       xfree (msg);
     }
 
@@ -333,7 +337,7 @@
   gpg_error_t err;
   const char *text1 = prompt;
   const char *text2 = _("Please re-enter this passphrase");
-  const char *initial_errtext = NULL;
+  char *initial_errtext = NULL;
   struct pin_entry_info_s *pi, *pi2;
 
   *r_passphrase = NULL;
@@ -371,10 +375,11 @@
 
  next_try:
   err = agent_askpin (ctrl, text1, NULL, initial_errtext, pi, NULL, 0);
+  xfree (initial_errtext);
   initial_errtext = NULL;
   if (!err)
     {
-      if (check_passphrase_constraints (ctrl, pi->pin, 0))
+      if (check_passphrase_constraints (ctrl, pi->pin, 0, &initial_errtext))
         {
           pi->failed_tries = 0;
           pi2->failed_tries = 0;
@@ -388,7 +393,7 @@
           if (err == -1)
             { /* The re-entered one did not match and the user did not
                  hit cancel. */
-              initial_errtext = _("does not match - try again");
+              initial_errtext = xstrdup ("does not match - try again");
               goto next_try;
             }
         }