diff --git a/functions/_tide_item_character.fish b/functions/_tide_item_character.fish
index 10bb324..1d76851 100644
--- a/functions/_tide_item_character.fish
+++ b/functions/_tide_item_character.fish
@@ -3,10 +3,12 @@ function _tide_item_character
 
     set -q add_prefix || echo -ns ' '
 
-    test "$fish_key_bindings" = fish_default_key_bindings && echo -ns $tide_character_icon ||
+    if test "$fish_key_bindings" = fish_default_key_bindings
+        test $_tide_status = 0 && echo -ns $tide_character_icon || echo -ns $tide_character_icon_failure
+    else
         switch $fish_bind_mode
             case insert
-                echo -ns $tide_character_icon
+                test $_tide_status = 0 && echo -ns $tide_character_icon || echo -ns $tide_character_icon_failure
             case default
                 echo -ns $tide_character_vi_icon_default
             case replace replace_one
@@ -14,4 +16,5 @@ function _tide_item_character
             case visual
                 echo -ns $tide_character_vi_icon_visual
         end
+    end
 end
diff --git a/functions/tide/configure/icons.fish b/functions/tide/configure/icons.fish
index a687bed..380638a 100644
--- a/functions/tide/configure/icons.fish
+++ b/functions/tide/configure/icons.fish
@@ -1,6 +1,7 @@
 tide_aws_icon  # Actual aws glyph is harder to see
 tide_bun_icon 󰳓
 tide_character_icon ❯
+tide_character_icon_failure ❯
 tide_character_vi_icon_default ❮
 tide_character_vi_icon_replace ▶
 tide_character_vi_icon_visual V
diff --git a/tests/_tide_item_character.test.fish b/tests/_tide_item_character.test.fish
new file mode 100644
index 0000000..8169c3c
--- /dev/null
+++ b/tests/_tide_item_character.test.fish
@@ -0,0 +1,180 @@
+# RUN: %fish %s
+_tide_parent_dirs
+
+function _character
+    set -lx _tide_status $status
+    set -lx _tide_pipestatus $pipestatus
+    _tide_decolor (_tide_item_character)
+end
+
+set -lx tide_character_icon_failure ✘
+
+# Check icons while fish_key_bindings is fish_default_key_bindings
+set -lx fish_key_bindings fish_default_key_bindings
+
+true
+_character # CHECK: ❯
+
+false
+_character # CHECK: ✘
+
+true | false
+_character # CHECK: ✘
+
+true | true
+_character # CHECK: ❯
+
+false | true
+_character # CHECK: ❯
+
+false | false
+_character # CHECK: ✘
+
+# Check that not command works
+not true | false
+_character # CHECK: ❯
+
+not false | true
+_character # CHECK: ✘
+
+# Check icons while fish_key_bindings isn't fish_default_key_bindings
+set -lx fish_key_bindings something_else
+# Check icons while fish_bind_mode is default
+set -lx fish_bind_mode default
+
+true
+_character # CHECK: ❮
+
+false
+_character # CHECK: ❮
+
+true | false
+_character # CHECK: ❮
+
+true | true
+_character # CHECK: ❮
+
+false | true
+_character # CHECK: ❮
+
+false | false
+_character # CHECK: ❮
+
+# Check that not command works
+not true | false
+_character # CHECK: ❮
+
+not false | true
+_character # CHECK: ❮
+
+# Check icons while fish_bind_mode is insert
+set -lx fish_bind_mode insert
+
+true
+_character # CHECK: ❯
+
+false
+_character # CHECK: ✘
+
+true | false
+_character # CHECK: ✘
+
+true | true
+_character # CHECK: ❯
+
+false | true
+_character # CHECK: ❯
+
+false | false
+_character # CHECK: ✘
+
+# Check that not command works
+not true | false
+_character # CHECK: ❯
+
+not false | true
+_character # CHECK: ✘
+
+# Check icons while fish_bind_mode is replace
+set -lx fish_bind_mode replace
+
+true
+_character # CHECK: ▶
+
+false
+_character # CHECK: ▶
+
+true | false
+_character # CHECK: ▶
+
+true | true
+_character # CHECK: ▶
+
+false | true
+_character # CHECK: ▶
+
+false | false
+_character # CHECK: ▶
+
+# Check that not command works
+not true | false
+_character # CHECK: ▶
+
+not false | true
+_character # CHECK: ▶
+
+# Check icons while fish_bind_mode is replace_one
+set -lx fish_bind_mode replace_one
+
+true
+_character # CHECK: ▶
+
+false
+_character # CHECK: ▶
+
+true | false
+_character # CHECK: ▶
+
+true | true
+_character # CHECK: ▶
+
+false | true
+_character # CHECK: ▶
+
+false | false
+_character # CHECK: ▶
+
+# Check that not command works
+not true | false
+_character # CHECK: ▶
+
+not false | true
+_character # CHECK: ▶
+
+# Check icons while fish_bind_mode is visual
+set -lx fish_bind_mode visual
+
+true
+_character # CHECK: V
+
+false
+_character # CHECK: V
+
+true | false
+_character # CHECK: V
+
+true | true
+_character # CHECK: V
+
+false | true
+_character # CHECK: V
+
+false | false
+_character # CHECK: V
+
+# Check that not command works
+not true | false
+_character # CHECK: V
+
+not false | true
+_character # CHECK: V