diff --git a/server/configs/application.properties b/server/configs/application.properties
index 6988270391..9f405cb8d7 100644
--- a/server/configs/application.properties
+++ b/server/configs/application.properties
@@ -32,6 +32,20 @@ context.validationQuery[0]=SELECT 1
 
 #useLocalBuild#context.webAppLocation=@@pathToServer@@/build/deploy/labkeyWebapp
 context.encryptionKey=@@encryptionKey@@
+
+# By default, we'll deploy to the root context path. However, some servers have historically used /labkey or even /cpas
+#context.contextPath=/labkey
+
+# Using a legacy context path provides backwards compatibility with old deployments. A typical use case would be to
+# deploy to the root context (the default) and configure /labkey as the legacy path. GETs will be redirected, and
+# non-GETs will be handled server-side via a servlet forward.
+#context.legacyContextPath=/labkey
+
+# Other webapps to be deployed, most commonly to deliver a set of static files. Additional
+# webapps can be specified via additional indices. docBase should point at the root of the webapp's content
+#webapps.contextPath[0]=/anotherWebapp
+#webapps.docBase[0]=/my/webapp/path
+
 #context.oldEncryptionKey=
 #context.requiredModules=
 #context.pipelineConfig=/path/to/pipeline/config/dir
diff --git a/server/embedded/src/org/labkey/embedded/LabKeyServer.java b/server/embedded/src/org/labkey/embedded/LabKeyServer.java
index 04d2f8b309..bddf870aa9 100644
--- a/server/embedded/src/org/labkey/embedded/LabKeyServer.java
+++ b/server/embedded/src/org/labkey/embedded/LabKeyServer.java
@@ -90,6 +90,12 @@ public JmsProperties jmsSource()
         return new JmsProperties();
     }
 
+    @Bean
+    public WebappProperties additionalWebappSource()
+    {
+        return new WebappProperties();
+    }
+
     @Bean
     public CSPFilterProperties cspSource()
     {
@@ -160,7 +166,7 @@ protected TomcatWebServer getTomcatWebServer(Tomcat tomcat)
                     }
 
                     // set the root path to the context explicitly
-                    context.setPath("");
+                    context.setPath(contextProperties.getContextPath());
 
                     // Push the JDBC connection for the primary DB into the context so that the LabKey webapp finds them
                     getDataSourceResources(contextProperties, context).forEach(contextResource -> context.getNamingResources().addResource(contextResource));
@@ -187,6 +193,14 @@ protected TomcatWebServer getTomcatWebServer(Tomcat tomcat)
                         context.addParameter("OldEncryptionKey", contextProperties.getOldEncryptionKey());
                     }
 
+                    if (contextProperties.getLegacyContextPath() != null)
+                    {
+                        if (contextProperties.getContextPath() != null && !contextProperties.getContextPath().isEmpty() && !contextProperties.getContextPath().equals("/"))
+                        {
+                            throw new IllegalArgumentException("contextPath.legacyContextPath is only intended for use when deploying the LabKey application to the root context path. Please update application.properties.");
+                        }
+                        context.addParameter("legacyContextPath", contextProperties.getLegacyContextPath());
+                    }
                     if (contextProperties.getRequiredModules() != null)
                     {
                         context.addParameter("requiredModules", contextProperties.getRequiredModules());
@@ -226,6 +240,18 @@ protected TomcatWebServer getTomcatWebServer(Tomcat tomcat)
                    configureJsonAccessLogging(tomcat, logConfig);
                 }
 
+                WebappProperties additionalWebapps = additionalWebappSource();
+                if (additionalWebapps.getContextPath().size() != additionalWebapps.getDocBase().size())
+                {
+                    throw new IllegalArgumentException("Additional webapps must have paired contextPath and docBase properties");
+                }
+                for (int i = 0; i < additionalWebapps.getContextPath().size(); i++)
+                {
+                    String contextPath = additionalWebapps.getContextPath().get(i);
+                    String docBase = additionalWebapps.getDocBase().get(i);
+                    tomcat.addWebapp(contextPath, docBase);
+                }
+
                 return super.getTomcatWebServer(tomcat);
             }
 
@@ -583,6 +609,35 @@ public void setConditionUnless(String conditionUnless)
         }
     }
 
+    @Configuration
+    @ConfigurationProperties("webapps")
+    public static class WebappProperties
+    {
+        private List<String> contextPath = new ArrayList<>();
+
+        private List<String> docBase = new ArrayList<>();
+
+        public List<String> getContextPath()
+        {
+            return contextPath;
+        }
+
+        public void setContextPath(List<String> contextPath)
+        {
+            this.contextPath = contextPath;
+        }
+
+        public List<String> getDocBase()
+        {
+            return docBase;
+        }
+
+        public void setDocBase(List<String> docBase)
+        {
+            this.docBase = docBase;
+        }
+    }
+
     @Validated
     @Configuration
     @ConfigurationProperties("context")
@@ -604,6 +659,10 @@ public static class ContextProperties
         @NotNull (message = "Must provide encryptionKey")
         private String encryptionKey;
         private String oldEncryptionKey;
+        private String legacyContextPath;
+
+        // Default to deploying to the root context path
+        private String contextPath = "";
         private String pipelineConfig;
         private String requiredModules;
         private boolean bypass2FA = false;
@@ -706,6 +765,26 @@ public void setOldEncryptionKey(String oldEncryptionKey)
             this.oldEncryptionKey = oldEncryptionKey;
         }
 
+        public String getLegacyContextPath()
+        {
+            return legacyContextPath;
+        }
+
+        public void setLegacyContextPath(String legacyContextPath)
+        {
+            this.legacyContextPath = legacyContextPath;
+        }
+
+        public String getContextPath()
+        {
+            return contextPath;
+        }
+
+        public void setContextPath(String contextPath)
+        {
+            this.contextPath = contextPath;
+        }
+
         public String getPipelineConfig()
         {
             return pipelineConfig;