Problem scenario
You want to install Octuopus Deploy (e.g., with the 45 free trial) to an AWS instance of Windows Server 2016. How do you do this?
Solution
This is a simple deployment of Octopus Deploy server for testing or evaluation purposes. Literally any AWS flavor will work as only 512 MB of RAM is needed for Octopus Deploy server to work for minimal evaluation.
1. Install SQL Server express.
a) Using Internet Explorer 11, go to Internet Options. Go to the Security tab. Click on "Internet." Scroll down to "Downloads." For "File download" (beneath "Downloads"), choose "Enable." Click "Ok" twice.
b) Go here. Scroll 60% of the way down. For the "SQL SErver 2016 SP1 Express" version, click "Download now."
c) There will be a small pop up near the bottom of the browser. Click "Run" to start.
d) For the "installation type" choose "Basic."
e) Read the license terms. If you can agree, click "Accept."
f) Leave the install location alone. Click "Install."
g) You may encounter "Download successful" with an apparent pause of a couple minutes with little information about the progress of the installation. The installation is not stuck. Just be patient. The installation process could take as much as 10 minutes. At the end, choose the option "Install SSMS."
h) Click the link for "Download SQL Server Management Studio 17.x."
i) Click "Save"
j) If you can agree to the License Terms and Privacy Statement, click "Install."
h) The process may take five to ten minutes. At the end a restart will be required. Click "Restart."
2. When the server reboots, Open SSMS. Right click "Databases" and click "New." For the "Database name" enter "foroctopus." Click "Ok."
3. Install Octopus Deploy.
a) (This first sub-step will allow the "Select platform" options buttons to actually appear in Internet Explorer 11. ) Using Internet Explorer 11, go to Internet Options. Go to the Security tab. Click on "Trusted sites." Set the "Security level for this zone" to be "Medium-low." Click "Sites" and add https://octopus.com. Click ok.
b) Download the Octopus Deploy MSI from this link: https://octopus.com/. Click "Select platform" under "Octopus server." Choose the option for Windows 64. Click "Save" to the window prompt that pops up.
c) Click "Run" once the .msi file has downloaded.
d) In the Setup Wizard (for Octopus Deploy Server), click "Next."
e) Read the End-User License Agreement. If you can agree, check the box for "I accept the terms..." and click "Next."
f) For the folder path of where to install Octopus, accept the default location by just clicking "Next."
g) Click "Install."
h) After a couple minutes, click "Finish."
i) At the "Welcome" screen, click "Get started."
j) Type in the requested info. You will need access to the email that is sent later on. Click the "Activate" button after you have typed in the information that they request.
k) For the "Home" directory, leave the default and click "Next."
l) Accept the default for the "Use Local System account" and click "Next."
m) For the "Database" page, click the "Server name" field. For the "Database" choose "foroctopus."
n) Click "Next."
o) You will get a pop up for "Add System account to Database." The prompt will say "In order to allow Octopus...we need to grant database access to the 'NT AUTHORITY\SYSTEM' account..." Click "OK" to grant access.
p) For the "Web Portal" prompt, just click "Next."
q) For the "Authentication" section, create an Octopus user with any username, password, and email of your choice. You will need the username and password later. Click "Next."
r) For "Installation" click "Install." This may take over 10 minutes. Be patient and eventually you will see "Installation successful. Happy deployments!" Click Finish.
s) You should see "Your Octopus server is ready to use!" Click "Open in browser." Internet Explorer will open. This may take five minutes for the web UI to load. You will see "The Octopus server is starting: Initializing database and performing migrations" and then a message about "Starting task scheduler." Just wait.
t) Enter the Username and Password you entered in step 2)q). Click "Sign in." This may take three to five minutes.
4) Undo the change made in step 3)a). Undo the changes made in step 1)a) if you want your AWS Windows server to be very secure. You are now done.