I can confirm that I can replicate this on my machine.

Setup
Host OS: fedora 27 workstation
Vagrant Version: vagrant 2.0.1
Vagrant Plugin List: vagrant-share 1.1.9, vagrant-vmware-workstation 5.0.4
VMWare Workstation: 14.1.1 build 7528167
Boxes used: bento/ubuntu-16.04, puppetlabs/ubuntu-16.04-64-nocm


On Tuesday, 2 January 2018 13:48:28 UTC-6, Lucas Rangit Magasweran wrote:
>
> Consistently, Vagrant boxes are stuck waiting for machine to boot until I 
> open the VMware Workstation GUI and leave it open. I'm using VMware 
> Workstation 12.5.7 on Ubuntu Linux 16.04 64-bit with Vagrant 2.0.0 and 
> provider plugin vagrant-vmware-workstation 5.0.1.
>
> This error is reproducible if I close the GUI and try to halt and up the 
> Vagrant box again. 
>
> Bringing machine 'default' up with 'vmware_workstation' provider...
> ==> default: Checking if box 'bento/ubuntu-16.04' is up to date...
> ==> default: Verifying vmnet devices are healthy...
> ==> default: Preparing network adapters...
> WARNING: The VMX file for this box contains a setting that is 
> automatically overwritten by Vagrant
> WARNING: when started. Vagrant will stop overwriting this setting in an 
> upcoming release which may
> WARNING: prevent proper networking setup. Below is the detected VMX 
> setting:
> WARNING: 
> WARNING:   ethernet0.pcislotnumber = "33"
> WARNING: 
> WARNING: If networking fails to properly configure, it may require this 
> VMX setting. It can be manually
> WARNING: applied via the Vagrantfile:
> WARNING: 
> WARNING:   Vagrant.configure(2) do |config|
> WARNING:     config.vm.provider :vmare_workstation do |vmware|
> WARNING:       vmware.vmx["ethernet0.pcislotnumber"] = "33"
> WARNING:     end
> WARNING:   end
> WARNING: 
> WARNING: For more information: https://
> www.vagrantup.com/docs/vmware/boxes.html#vmx-whitelisting
> ==> default: Fixed port collision for 22 => 2222. Now on port 2200.
> ==> default: Starting the VMware VM...
> ==> default: Waiting for the VM to receive an address...
> ==> default: Forwarding ports...
>     default: -- 22 => 2200
> ==> default: Waiting for machine to boot. This may take a few minutes...
>
> Stuck here waiting until I open VMware Workstation GUI console. The 
> following is the output after opening the GUI.
>
>     default: SSH address: 127.0.0.1:2200
>     default: SSH username: vagrant
>     default: SSH auth method: private key
> ==> default: Machine booted and ready!
> ==> default: Configuring network adapters within the VM...
> ==> default: Waiting for HGFS to become available...
> ==> default: Enabling and configuring shared folders...
>     default: -- /home/user/code: /vagrant
>     default: -- /home/user/Downloads: /vagrant_data
> ==> default: Machine already provisioned. Run `vagrant provision` or use 
> the `--provision`
> ==> default: flag to force provisioning. Provisioners marked to run 
> always will still run.
>
>
>

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