diff --git a/lib/utils.bash b/lib/utils.bash
index 21978a929..3f2038c62 100644
--- a/lib/utils.bash
+++ b/lib/utils.bash
@@ -803,6 +803,7 @@ with_shim_executable() {
   (
     local preset_plugin_versions
     preset_plugin_versions=()
+    local preset_plugin_installed=
     local closest_tool_version
     closest_tool_version=$(find_tool_versions)
 
@@ -815,22 +816,32 @@ with_shim_executable() {
       IFS=' ' read -r -a shim_versions <<<"$version_string"
       local usable_plugin_versions
       for shim_version in "${shim_versions[@]}"; do
-        preset_plugin_versions+=("$shim_plugin $shim_version")
+        if grep -q "$shim_version" <<<"$(asdf list "$shim_plugin")"; then
+          preset_plugin_installed="yes"
+        else
+          preset_plugin_versions+=("$shim_plugin $shim_version")
+        fi
       done
     done
 
-    if [ -n "${preset_plugin_versions[*]}" ]; then
-      printf "%s %s\n" "No preset version installed for command" "$shim_name"
-      printf "%s\n\n" "Please install a version by running one of the following:"
-      for preset_plugin_version in "${preset_plugin_versions[@]}"; do
-        printf "%s %s\n" "asdf install" "$preset_plugin_version"
-      done
-      printf "\n%s %s\n" "or add one of the following versions in your config file at" "$closest_tool_version"
+    if [ -n "$preset_plugin_installed" ]; then
+      printf "%s '%s' %s\n" "Shimmed command" "$shim_name" "has no matched plugin version"
+      printf "%s %s %s\n" "Check the executable or try install" "$shim_name" "for your preset plugin version"
     else
-      printf "%s %s\n" "No version is set for command" "$shim_name"
-      printf "%s %s\n" "Consider adding one of the following versions in your config file at" "$closest_tool_version"
+      if [ -n "${preset_plugin_versions[*]}" ]; then
+        printf "%s %s\n" "No preset version installed for command" "$shim_name"
+        printf "%s\n\n" "Please install a version by running one of the following:"
+        for preset_plugin_version in "${preset_plugin_versions[@]}"; do
+          printf "%s %s\n" "asdf install" "$preset_plugin_version"
+        done
+        printf "\n%s %s\n" "or add one of the following versions in your config file at" "$closest_tool_version"
+        shim_plugin_versions "${shim_name}"
+      else
+        printf "%s %s\n" "No version is set for command" "$shim_name"
+        printf "%s %s\n" "Consider adding one of the following versions in your config file at" "$closest_tool_version"
+        shim_plugin_versions "${shim_name}"
+      fi
     fi
-    shim_plugin_versions "${shim_name}"
   ) >&2
 
   return 126
diff --git a/test/shim_exec.bats b/test/shim_exec.bats
index 5c6d0673e..0c4860bef 100644
--- a/test/shim_exec.bats
+++ b/test/shim_exec.bats
@@ -129,6 +129,29 @@ teardown() {
   echo "$output" | grep -q "dummy 1.0" 2>/dev/null
 }
 
+@test "shim exec should suggest to check obsolete shim" {
+  # Install 1.0, with fake "dummyman" command, shimmed for 1.0
+  run asdf install dummy 1.0
+  echo "echo Dummy Manager" >"$ASDF_DIR/installs/dummy/1.0/bin/dummyman"
+  chmod +x "$ASDF_DIR/installs/dummy/1.0/bin/dummyman"
+  run asdf reshim dummy 1.0
+
+  # Install 1.3
+  run asdf install dummy 1.3
+  echo "dummy 1.3" >"$PROJECT_DIR/.tool-versions"
+
+  # reshim doesn't help
+  run asdf reshim dummy
+  run asdf shim-versions dummyman
+  [ "$status" -eq 0 ]
+  [ "$output" = "dummy 1.0" ]
+  run "$ASDF_DIR/shims/dummyman"
+  [ "$status" -eq 126 ]
+
+  echo "$output" | grep -q "Shimmed command 'dummyman' has no matched plugin version" 2>/dev/null
+  echo "$output" | grep -q "Check the executable or try install dummyman for your preset plugin version" 2>/dev/null
+}
+
 @test "shim exec should execute first plugin that is installed and set" {
   run asdf install dummy 2.0.0
   run asdf install dummy 3.0