Worst WTF dev experience? The login process from hell to a well-fortified dev environment at a client's site.
I assume a noob admin found a list of security tips and just went like "all of the above!".

You boot a Linux VM, necessary to connect to their VPN. Why necessary? Because 1) their VPN is so restrictive it has no internet access 2) the VPN connection prevents *your local PC* from accessing the internet as well. Coworkers have been seen bringing in their private laptops just to be able to google stuff.
So you connect via Cisco AnyConnect proprietary bullshit. A standard VPN client won't work. Their system sends you a one-time key via SMS as your password.

Once on their VPN, you start a remote desktop session to their internal "hopping server", which is a Windows server. After logging in with your Windows user credentials, you start a Windows Remote Desktop session *on that hopping server* to *another* Windows server, where you login with yet another set of Windows user credentials. For all these logins you have 30 seconds, otherwise back to step 1.
On that server you open a browser to access their JIRA, GitLab, etc or SSH into the actual dev machines - which AGAIN need yet another set of credentials.

So in total: VM -> VPN + RDP inside VM -> RDP #2 -> Browser/SSH/... -> Final system to work on
Input lag of one to multiple seconds. It was fucking unusable.

Now, the servers were very disconnect-happy to prevent anything "fishy" going on. Sitting at my desk at my company, connected to my company's wifi, was apparently fishy enough to kick me out every 5 to 20 minutes. And that meant starting from step 1 inside the VM again. So, never forget to plugin your network cable.

There's a special place in hell for this admin. And if there isn't, I'll PERSONALLY make the devil create one. Even now that I'm not even working on this any more.

@netikras since when does proprietary mean bad?

Lemme tell you 3 stories.

CISCO AnyConnect:
- come in to the office
- use internal resources (company newsletter, jira, etc.)
- connect to client's VPN using Cisco AnyConnect
- lose access to my company resources, because AnyConnect overwrites routing table (rather normal for VPN clients)
- issue a route command updating routing table so you could reach confluence page in the intranet
- route command executes successfully, `route -n` shows nothing has changed
- google this whole WTF case
- Cisco AnyConnect constantly overwrites OS routing table to ENFORCE you to use VPN settings and nothing else.

Sooo basically if you want to check your company's email, you have to disconnect from client's VPN, check email and reconnect again. Neat!

Can be easily resolved by using opensource VPN client -- openconnect

CISCO AnyConnect:
- get a server in your company
- connect it to client's VPN and keep the VPN running for data sync. VPN has to be UP at all times
- network glitch [uh-oh]
- VPN is no longer working, AnyConnect still believes everything is peachy. No reconnect attempts.
- service is unable to sync data w/ client's systems. Data gets outdated and eventually corrupted

OpenConnect (OSS alternative to AnyConnect) detects all network glitches, reports them to the log and attempts reconnect immediatelly. Subsequent reconnect attempts getting triggered with longer delays to not to spam network.

SYMANTEC VIP (alleged 2FA?):
- client's portal requires Sym VIP otp code to log in
- open up a browser in your laptop
- navigate to the portal
- enter your credentials
- click on a Sym VIP icon in the systray
- write down the shown otp number
- log in

umm... in what fucking way is that a secure 2FA? Everything is IN the same fucking device, a single click away.

Can be easily solved by opensource alternatives to Sym VIP app: they make HTTP calls to Symantec to register a new token and return you the whole totp url. You can convert that url to a qr code and scan it w/ your phone (e.g. Google's Authenticator). Now you have a true 2FA.

Proprietary is not always bad. There are good propr sw too. But the ones that are core to your BAU and are doing shit -- well these ARE bad. and w/o an oppurtunity to workaround/fix it yourself.

Got drunk during work time because fuck openvpn, fuck anyconnect, and fuck badly designed vpn servers in general.

A fucking pptp connection, man, a fucking pptp.

Cisco Anyconnect can blow me.

I go through the process of connecting to the vpn, username, password, token.

Then it has its pop up "respond to the banner to connect" and I click accept . . . and it does nothing.

So I go through the process again. And this time it says connected

But now I still can't connect to any of my companies sharepoint, SQL servers, Azure Devops, JIRA, etc

And the only solution to that is a reboot.

And this happens swear to god at least every other day.

Like good lord, if I put in my credentials and they pass authentication/authorization, let me do my goddamn work.