Not Communicating with Server - Windows Server 2012 R2

I set up a new version of Octoprint on a Windows Server. Everything looks like it's running ok. But it completely freezes when I attempt to connect to it. I've tried http://127.0.0.1:5000/ from the server itself and ip:5000 from a remote computer and neither work. Is there something wrong that I've done in the setup?

Microsoft Windows [Version 6.3.9600]
(c) 2013 Microsoft Corporation. All rights reserved.

C:\Windows\System32>C:\OctoPrint\venv\Scripts\octoprint.exe serve
2019-06-04 16:01:17,076 - octoprint.startup - INFO - ***************************
***************************************************
2019-06-04 16:01:17,079 - octoprint.startup - INFO - Starting OctoPrint 1.3.11
2019-06-04 16:01:17,081 - octoprint.startup - INFO - Starting in SAFE MODE. Thir
d party plugins will be disabled!
2019-06-04 16:01:17,082 - octoprint.startup - INFO - Reason for safe mode: probl
em during last startup
2019-06-04 16:01:17,082 - octoprint.startup - INFO - ***************************
***************************************************
2019-06-04 16:01:17,395 - octoprint.plugin.core - INFO - Loading plugins from c:
\octoprint\venv\lib\site-packages\octoprint\plugins, C:\Users\Administrator.BT-W
S\AppData\Roaming\OctoPrint\plugins and installed plugin packages...
2019-06-04 16:01:18,779 - octoprint.plugin.core - INFO - Plugin Pi Support Plugi
n did not pass check, not loading.
2019-06-04 16:01:18,951 - octoprint.plugins.octoprint.plugins.discovery - INFO -
 pybonjour is not installed, Zeroconf Discovery won't be available
2019-06-04 16:01:18,961 - octoprint.plugin.core - INFO - Found 14 plugin(s) prov
iding 14 mixin implementations, 22 hook handlers
2019-06-04 16:01:19,042 - octoprint.server.heartbeat - INFO - Starting server he
artbeat, 900.0s interval
2019-06-04 16:01:19,273 - octoprint.server - INFO - Intermediary server started
2019-06-04 16:01:19,273 - octoprint.plugin.core - INFO - Loading plugins from c:
\octoprint\venv\lib\site-packages\octoprint\plugins, C:\Users\Administrator.BT-W
S\AppData\Roaming\OctoPrint\plugins and installed plugin packages...
2019-06-04 16:01:19,286 - octoprint.plugin.core - INFO - Plugin Pi Support Plugi
n did not pass check, not loading.
2019-06-04 16:01:19,354 - octoprint.plugin.core - INFO - Found 14 plugin(s) prov
iding 14 mixin implementations, 22 hook handlers
2019-06-04 16:01:19,381 - octoprint.filemanager.storage - INFO - Initializing th
e file metadata for C:\Users\Administrator.BT-WS\AppData\Roaming\OctoPrint\uploa
ds...
2019-06-04 16:01:19,384 - octoprint.filemanager.storage - INFO - ... file metada
ta for C:\Users\Administrator.BT-WS\AppData\Roaming\OctoPrint\uploads initialize
d successfully.
2019-06-04 16:01:20,332 - octoprint.util.pip - INFO - Using "c:\octoprint\venv\s
cripts\python.exe -m pip" as command to invoke pip
2019-06-04 16:01:21,424 - octoprint.util.pip - INFO - Version of pip is 19.1.1
2019-06-04 16:01:21,426 - octoprint.util.pip - INFO - pip installs to c:\octopri
nt\venv\Lib\site-packages (writable -> yes), --user flag needed -> no, virtual e
nv -> yes
2019-06-04 16:01:21,427 - octoprint.util.pip - INFO - ==> pip ok -> yes
2019-06-04 16:01:21,430 - octoprint.plugin.core - INFO - Initialized 14 plugin i
mplementation(s)
2019-06-04 16:01:21,434 - octoprint.plugin.core - INFO - 14 plugin(s) registered
 with the system:
|  Action Command Prompt Support (bundled) = c:\octoprint\venv\lib\site-packages
\octoprint\plugins\action_command_prompt
|  Announcement Plugin (bundled) = c:\octoprint\venv\lib\site-packages\octoprint
\plugins\announcements
|  Anonymous Usage Tracking (bundled) = c:\octoprint\venv\lib\site-packages\octo
print\plugins\tracking
|  Application Keys Plugin (bundled) = c:\octoprint\venv\lib\site-packages\octop
rint\plugins\appkeys
|  Backup & Restore (bundled) = c:\octoprint\venv\lib\site-packages\octoprint\pl
ugins\backup
|  Core Wizard (bundled) = c:\octoprint\venv\lib\site-packages\octoprint\plugins
\corewizard
|  Discovery (bundled) = c:\octoprint\venv\lib\site-packages\octoprint\plugins\d
iscovery
|  Error Tracking (bundled) = c:\octoprint\venv\lib\site-packages\octoprint\plug
ins\errortracking
|  Force Login (bundled) = c:\octoprint\venv\lib\site-packages\octoprint\plugins
\forcelogin
|  Logging (bundled) = c:\octoprint\venv\lib\site-packages\octoprint\plugins\log
ging
|  Plugin Manager (bundled) = c:\octoprint\venv\lib\site-packages\octoprint\plug
ins\pluginmanager
|  Printer Safety Check (bundled) = c:\octoprint\venv\lib\site-packages\octoprin
t\plugins\printer_safety_check
|  Software Update (bundled) = c:\octoprint\venv\lib\site-packages\octoprint\plu
gins\softwareupdate
|  Virtual Printer (bundled) = c:\octoprint\venv\lib\site-packages\octoprint\plu
gins\virtual_printer
2019-06-04 16:01:21,444 - octoprint.environment - INFO - Detected environment is
 Python 2.7.16 under Windows (win32). Details:
|  hardware:
|    cores: 4
|    freq: 3700.0
|    ram: 8461086720
|  os:
|    id: windows
|    platform: win32
|  python:
|    pip: 19.1.1
|    version: 2.7.16
|    virtualenv: c:\octoprint\venv
2019-06-04 16:01:21,450 - octoprint.server - INFO - Reset webasset folder C:\Use
rs\Administrator.BT-WS\AppData\Roaming\OctoPrint\generated\webassets...
2019-06-04 16:01:21,451 - octoprint.server - INFO - Reset webasset folder C:\Use
rs\Administrator.BT-WS\AppData\Roaming\OctoPrint\generated\.webassets-cache...
2019-06-04 16:01:21,967 - octoprint.server - INFO - Shutting down intermediary s
erver...
2019-06-04 16:01:22,275 - octoprint.server - INFO - Intermediary server shut dow
n
2019-06-04 16:01:22,279 - octoprint.events - INFO - Processing startup event, th
is is our first event
2019-06-04 16:01:22,280 - octoprint.events - INFO - Adding 0 events to queue tha
t were held back before startup event
2019-06-04 16:01:22,286 - octoprint.filemanager - INFO - Adding backlog items fr
om all storage types to analysis queue...
2019-06-04 16:01:22,292 - octoprint.filemanager - INFO - Added 0 items from stor
age type "local" to analysis queue
2019-06-04 16:01:22,292 - octoprint.server.util.watchdog - INFO - Running initia
l scan on watched folder...
2019-06-04 16:01:22,296 - octoprint.server.util.watchdog - INFO - ... initial sc
an done.
2019-06-04 16:01:22,308 - octoprint.plugins.discovery - INFO - Registered OctoPr
int instance on BT-WS for SSDP
2019-06-04 16:01:22,335 - octoprint.server - INFO - Listening on http://0.0.0.0:
5000 and http://[::]:5000

Locally on the server, open up a Bash/POSIX shell and run:

curl http://localhost:5000/

...and see what you get back. The main OctoPrint server appears to be running, for what it's worth. If this fails to retrieve some HTML then you might want to visit the software firewall (or whatever they're calling it these days) to make sure that the server can publish ports 5000 and 80.

You didn't mention whether or not you also installed haproxy. That would be the part which serves the port 5000 over to the default ports 80 (http) and 443 (https).

For what it's worth, you've installed OctoPrint into the global space (the root of the C: drive) which Microsoft really doesn't want you to do. They want you to install it into C:\Program Files, C:\Program Files (x86) or into C:\Users\pi. I also see something from C:\Users\Administrator and it's usually bad form to install any web services like this to run under the security context of Administrator. Imagine what could happen if a plugin author decided to go rogue?

Thanks for the feedback. I will test the curl tonight. But I did follow the instructions here (Setting up OctoPrint on Windows), which had it in C:\OctoPrint in step 4. I understand the risk that you're describing, I just wanted to get through a working installation before deviating from the instructions.

For what its worth, the only other things I have installed on my server at home are Unifi Network Controller and Plex.

You might want to make sure that ports 80, 443 and 5000 aren't already in use on your server. If so, then you might need to disable any services already using them. In the Microsoft world one would run netstat -an | find "LISTEN" to look for any bound ports. Once you see some output from that you could do netstat -an | find "LISTEN" | find "80" to just see a single port.

So I think its something with the preemptive cache? Looking at this, it seems like its making a connection, but something is hitting a wall (https://imgur.com/0LgxZTV).

By my read of the log, the preemptive cache is just doing its thing. The final line was a 401 returned from the Access Control plugin, it would seem.

You might try to do a hard-refresh on your browser to make sure that it's not using old cached data. Or possibly it's cookie-related. But then again, you didn't give the output of the curl command from earlier.