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I would like to run a web server and storage server while still having the raspbian stretch over VNC. How would I go about setting up a web server and storage server off of raspbian with the storage server having a 2tb external HDD and several users? All clients are running MS Windows.

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    The headless element looks totally irrelevant here. Same with the Pi. You would go about it the same as on any other Linux computer
    – Dirk
    Mar 6, 2019 at 18:59
  • What OS types will be the storage server clients? (e.g. Windows PC vs. other Linux or Unix hosts such as other Raspberry Pi's, other Linux hosts, or macOS clients.) "how" you setup the storage server depends on which network filesystem type (e.g. Samba vs. NFS) you need to use. (Samba for Windows, NFS for Unix/Linux) Mar 6, 2019 at 18:59
  • I would like to use it for windows. Sorry for not specifying! Mar 6, 2019 at 19:17
  • web server - you need one of apache, nginx or even lighttpd Mar 6, 2019 at 22:34

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For the web server, as others have said it is a choice between apache, nginx or lighttpd depending on your use case.

For the storage server with windows clients this is exactly what Samba is designed to for.

First you have to mount the 2tb external HDD. To do that follow this guide:

Connect your Raspberry Pi to a USB hard disk

Then you need to install and set up Samba. Samba is a very complex suite of software, with lots of options. But here is a simple guide to get you going;

Share your Raspberry Pi's files and folders across a network

With multiple windows users the Microsoft way is to have an Active Directory Domain Controller ADDC to handle authentication. Samba4 includes its own ADDC, but it is well beyond this answer to cover the set up of an ADDC. For a small group of users it may be simpler to create users using smbpassword described in the second link. Just watch the linux file and folder permissions on the pi, to make sure each user can read/write to the folders on the pi.

HTH

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