Will pihole + openVPN + stunnel work?

On windows using putty or?
If it's with putty, select telnet, put in port 445 and ip address of pi. Blank screen.

In a DOS command box.

Welcome to Microsoft Telnet Client

Escape Character is 'CTRL+]'

Am missing bottom bit if I do same on Windows client ?

Welcome to Microsoft Telnet Client

Escape Character is 'CTRL+]'

Microsoft Telnet>
C:\>

No connection failed errors ?

There's no bottom bit of Microsoft Telnet>

No connection errors, I paste whatever is there, I leave nothing out.


Suppose to see the raspberrypi computer over OpenVPN.

I do remember that when I used the pivpn installer this worked. Now for the sake of stunnel I had to manually config the VPN myself. Everything seems to work perfectly, only now the smb share isn't showing up like before.

Ok, I am out of ideas.

So I first did:

sudo apt-get install nginx openssl ssl-cert php5-cli php5-sqlite php5-gd php5-common php5-cgi sqlite3 php-pear php-apc curl libapr1 libtool curl libcurl4-openssl-dev php-xml-parser php5 php5-dev php5-curl php5-gd php5-fpm memcached php5-memcache varnish

And then I thought I didn't need those packages anymore so I did:
sudo apt-get purge nginx openssl ssl-cert php5-cli php5-sqlite php5-gd php5-common php5-cgi sqlite3 php-pear php-apc curl libapr1 libtool curl libcurl4-openssl-dev php-xml-parser php5 php5-dev php5-curl php5-gd php5-fpm memcached php5-memcache varnish

And now sudo apt-get dist-upgrade -y won't work and I get a bunch of dependency issues. Know how to fix this mess? Lol..I'm screwed..

Trying apt-get -f install doesn't work

EDIT: If dependency issues are too hard (or troublesome) to fix, then I guess I'll have to purge the entire server and install a fresh raspbian jesse on it ! Always works..but I hope not because generating another dh4096.pem can take about 1.5 days !

You should have never run this one (and you dont need to run it ever ... mostly).
You could try re-installing the dependencies.
But changes are, the dist upgrade screwed up things that much, that it might be quicker to reinstall.

Cant you copy over the certificates?
EDIT: They are mostly hostname based so if keep same hostname, you should be able to use the same PEM's.

Oh great ! Didn't know the PEMs are only hostname based. Sure I'll just use it so my reinstall would be quick.

I did try installing what is dependent according to the terminal output, but every package seems to depend on another, it's just a mess.

Definitely reinstalling a fresh jesse.

That's interesting stuff, could you explain a little more? Cause I see this command commonly run in youtube tutorials, thought it was a common thing like apt-get update?

Okay, got everything up and running..

So I have openVPN, stunnel, samba, nextcloud, and transmission-daemon all running harmoniously on my raspberry pi.

Last thing and I'm done with this thread, how do you did about my openVPN server.conf? I followed various guides on securing and hardening the VPN. Anything else you suggest I add to it to make it more secure?

port 666
proto tcp
dev tun
ca /etc/openvpn/easy-rsa/keys/ca.crt
cert /etc/openvpn/easy-rsa/keys/VPN-Server.crt
key /etc/openvpn/easy-rsa/keys/VPN-Server.key
dh /etc/openvpn/easy-rsa/keys/dh4096.pem
server 10.8.0.0 255.255.255.0
push "redirect-gateway def1 bypass-dhcp"
push "dhcp-option DNS 8.8.8.8"
push "dhcp-option DNS 8.8.4.4"
keepalive 10 120
tls-auth /etc/openvpn/easy-rsa/keys/ta.key 0
tls-version-min 1.2
crl-verify /etc/openvpn/crl.pem
remote-cert-tls client
auth SHA512
cipher AES-256-CBC
comp-lzo
user nobody
group nogroup
persist-key
persist-tun
status /var/log/openvpn-status.log
verb 3

EDIT: Updated to openVPN 2.4.3 and added a bunch of security stuff...this thread's concluded I guess...

Thanks @Anudeep and @deHakkelaar for your help ! Both of you have been really helpful !

A dist-upgrade will install and uninstall packages that sometimes would not be desired.
Configuration files might get overwritten with new ones.
It just tries to upgrade no matter what:

Nice everything working for you now :+1: