diff --git a/builder/vmware/common/run_config.go b/builder/vmware/common/run_config.go
index e79bf20ea..a649ae4c8 100644
--- a/builder/vmware/common/run_config.go
+++ b/builder/vmware/common/run_config.go
@@ -14,6 +14,11 @@ type RunConfig struct {
 	// this value is set to true, the machine will start without a console. For
 	// VMware machines, Packer will output VNC connection information in case you
 	// need to connect to the console to debug the build process.
+	// Some users have experienced issues where Packer cannot properly connect
+	// to a VM if it is headless; this appears to be a result of not ever having
+	// launched the VMWare GUI and accepting the evaluation license, or
+	// supplying a real license. If you experience this, launching VMWare and
+	// accepting the license should resolve your problem.
 	Headless bool `mapstructure:"headless" required:"false"`
 	// The IP address that should be
 	// binded to for VNC. By default packer will use 127.0.0.1 for this. If you
diff --git a/website/pages/partials/builder/vmware/common/RunConfig-not-required.mdx b/website/pages/partials/builder/vmware/common/RunConfig-not-required.mdx
index e3226dca6..79212e926 100644
--- a/website/pages/partials/builder/vmware/common/RunConfig-not-required.mdx
+++ b/website/pages/partials/builder/vmware/common/RunConfig-not-required.mdx
@@ -5,6 +5,11 @@
     this value is set to true, the machine will start without a console. For
     VMware machines, Packer will output VNC connection information in case you
     need to connect to the console to debug the build process.
+    Some users have experienced issues where Packer cannot properly connect
+    to a VM if it is headless; this appears to be a result of not ever having
+    launched the VMWare GUI and accepting the evaluation license, or
+    supplying a real license. If you experience this, launching VMWare and
+    accepting the license should resolve your problem.
     
 -   `vnc_bind_address` (string) - The IP address that should be
     binded to for VNC. By default packer will use 127.0.0.1 for this. If you