diff --git a/lib/ykpiv.c b/lib/ykpiv.c
index 427ce89..7936ee2 100644
--- a/lib/ykpiv.c
+++ b/lib/ykpiv.c
@@ -808,10 +808,10 @@ ykpiv_rc ykpiv_import_private_key(ykpiv_state *state, const unsigned char key, u
   if (state == NULL)
     return YKPIV_GENERIC_ERROR;
 
-  if (key != YKPIV_KEY_AUTHENTICATION &&
-      key != YKPIV_KEY_SIGNATURE &&
-      key != YKPIV_KEY_KEYMGM &&
-      key != YKPIV_KEY_CARDAUTH) {
+  if (key == YKPIV_KEY_CARDMGM ||
+      key < YKPIV_KEY_RETIRED1 ||
+      (key > YKPIV_KEY_RETIRED20 && key < YKPIV_KEY_AUTHENTICATION) ||
+      key > YKPIV_KEY_CARDAUTH) {
     return YKPIV_KEY_ERROR;
   }
 
diff --git a/lib/ykpiv.h b/lib/ykpiv.h
index 16b92a2..a868966 100644
--- a/lib/ykpiv.h
+++ b/lib/ykpiv.h
@@ -111,6 +111,26 @@ extern "C"
 #define YKPIV_KEY_SIGNATURE 0x9c
 #define YKPIV_KEY_KEYMGM 0x9d
 #define YKPIV_KEY_CARDAUTH 0x9e
+#define YKPIV_KEY_RETIRED1 0x82
+#define YKPIV_KEY_RETIRED2 0x83
+#define YKPIV_KEY_RETIRED3 0x84
+#define YKPIV_KEY_RETIRED4 0x85
+#define YKPIV_KEY_RETIRED5 0x86
+#define YKPIV_KEY_RETIRED6 0x87
+#define YKPIV_KEY_RETIRED7 0x88
+#define YKPIV_KEY_RETIRED8 0x89
+#define YKPIV_KEY_RETIRED9 0x8a
+#define YKPIV_KEY_RETIRED10 0x8b
+#define YKPIV_KEY_RETIRED11 0x8c
+#define YKPIV_KEY_RETIRED12 0x8d
+#define YKPIV_KEY_RETIRED13 0x8e
+#define YKPIV_KEY_RETIRED14 0x8f
+#define YKPIV_KEY_RETIRED15 0x90
+#define YKPIV_KEY_RETIRED16 0x91
+#define YKPIV_KEY_RETIRED17 0x92
+#define YKPIV_KEY_RETIRED18 0x93
+#define YKPIV_KEY_RETIRED19 0x94
+#define YKPIV_KEY_RETIRED20 0x95
 
 #define YKPIV_OBJ_CAPABILITY 0x5fc107
 #define YKPIV_OBJ_CHUID 0x5fc102
diff --git a/tool/yubico-piv-tool.c b/tool/yubico-piv-tool.c
index 8989667..fb521b9 100644
--- a/tool/yubico-piv-tool.c
+++ b/tool/yubico-piv-tool.c
@@ -445,7 +445,6 @@ static bool import_key(ykpiv_state *state, enum enum_key_format key_format,
         goto import_out;
       }
 
-      ret = true;
       rc = ykpiv_import_private_key(state, key, algorithm,
                                     NULL, 0,
                                     NULL, 0,
@@ -456,6 +455,7 @@ static bool import_key(ykpiv_state *state, enum enum_key_format key_format,
                                     pp, tp);
     }
 
+    ret = true;
     if(rc != YKPIV_OK) {
       ret = false;
     }
@@ -1822,6 +1822,7 @@ int main(int argc, char *argv[]) {
       case action_arg_importMINUS_key:
         if(import_key(state, args_info.key_format_arg, args_info.input_arg, args_info.slot_orig, args_info.password_arg,
               args_info.pin_policy_arg, args_info.touch_policy_arg) == false) {
+          fprintf(stderr, "Unable to import private key\n");
           ret = EXIT_FAILURE;
         } else {
           fprintf(stderr, "Successfully imported a new private key.\n");