So, you have some new FileMaker databases that you need to upload to FileMaker Server. You go ahead and want to upload them via FileMaker Pro, but you get a “connection failed” message. First, you might double check your login credentials and sure enough, they are correct. You try again, no luck…
Hmmm, what could be causing that you might wonder, scratching your head after several attempts from different machines on the same network. You might have also tried to upload them via FileMaker Pro to FileMaker Server on the same machine, but still the same dreaded “connection failed” message…
Doesn’t make sense, as you already have databases hosted on your FileMaker Server and they can be accessed from your FileMaker Pro clients with no problems. So, you also check to make sure any security software wasn’t blocking the upload, still no luck!
Well, we recently had the same problem for a client and after multiple tries and some frustration, we called FileMaker Support. The answer to the conundrum was that you need to have both port 443 available (FileMaker Server needs port 80 and port 443 available for install) and Web Server needs to be enabled at the same time. Web Server which is IIS for Windows and Apache for Mac, not to be confused with Web Publishing Service. Without Web Server being enabled and port 443 available for FileMaker Server, you will not be able to make a connection and upload your databases with FileMaker Pro, no matter if you try to upload via FileMaker Pro on the actual host machine or any other FileMaker Pro client machine.
So, this is how you can go about making sure that Web Server is enabled and running.
Windows
Open the Internet Information Services (IIS) Manager and find the select “Sites”. Here you should see “FMWebSite” that will use port 80 for HTTP and port 443 for HTTPS with a status of Started or Stopped, if it says stopped then this is the reason why you are unable to upload databases through FileMaker Pro upload function. The images below are samples and shows you how to enable Web Server for FileMaker again.

Mac OS
FileMaker Server installer creates its own instance of the Apache web server, and FileMaker Server uses port 80 for HTTP and port 443 for HTTPS. You can easily check if the instance of Web Server for FileMaker Server is running. Open Safari and type in localhost in the address field, press enter. If you get the image below then Web Server is running and you should have no problem uploading databases with FileMaker Pro.

If not then you have to run a command in terminal that will restart the FMS instance of Apache, re-claiming port 80 and 443.
Open up terminal and run the following command:
sudo /Library/FileMaker\ Server/HTTPServer/bin/httpdctl graceful
Type in your admin password and this is the screen you will get after, the Apache instance for FileMaker Server should now be running and you can upload databases through FileMaker Pro.

You might also want to check that the firewall on the machine that has FileMaker Server running on it has port 443 open as well, especially if you try and upload from another machine than the one that FileMaker Server is running on. This port (443) needs to be open for an upload to work if a firewall is active.
So, after you have enabled Web Server, this is the screen you should see instead of the “connection failed message.
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