Thx everyone for the great replies.

I decided to take Konstantin Kolinko's advice and start a new installation from 
scratch using tomcat-8.5.32.

I have had some success, but still can't deploy WARS.

Here is what I did:

== Step 1: Installing Tomcat per se ==
I used the instructions on this page:

* Download the zip file and unzip it on your HD under 
/usr/local/apache-tomcat-N.N.N (where N.N.N is the version number).
** Note: In the rest of this document, that directory will be referred to 
* Create a symlink /Library/Tomcat to make managing future versions easier:
        sudo rm -f /Library/Tomcat
        sudo ln -s [CATALINA_HOME] /Library/Tomcat
* Change ownership of /Library/Tomcat
        sudo chown -R <your_username> /Library/Tomcat
* Make all scripts executable
        sudo chmod +x /Library/Tomcat/bin/*.sh
* Now, I can start/stop tomcat as follows:
     Especially ‘’, as this will end up creating a bunch of temporay 
dirs and files that will be owned by ROOT, and cannot be written unless you 
start Tomcat as ROOT.
* Test the installation by:
** Starting Tomcat with
** Pointing my browser at http://localhost:8080/.
** I see the Tomcat home page no problem

== Step 2: Configuring the Tomcat Manager Apps ==

* Edit the file /Library/Tomcat/conf/tomcat-users.xml, and add the following 
lines inside the <tomcat-users> tag pair:

        <role rolename="admin-gui"/>
        <role rolename="manager-gui"/>
        <user username="admin" password="PASSWORD" 

* Shutdown and re-start Tomcat
* At this point, I can click on any of the following buttons: 'Server Status', 
'Manager' App, 'Host Manager' and once I enter the user and passwords I 
specified in <tomcat-users>, I get to see the corresponding page.
** On 'Manager App', I was able to start, stop, re-deploy EXISTING apps.
** BUT....
*** When I tried to deploy a new WAR file, I got:

        This site can’t be reached
        The connection was reset.

                Checking the connection
                Checking the proxy and the firewall

After a bit of reading, it seems that this is because the WAR file I was 
deploying was larger than the maximum size allowed. I fixed that by editing 
/Library/Tomcat/webapps/manager/WEB-INF/web.xml, and changing the size in the 
following tags:

        <max-file-size>50000000 </max-file-size>
        <max-request-size>50000000 </max-request-size>

And now, all seem to work fine.

Again, thanks to everyone who pitched in with some advice. It was really 


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