diff --git a/templates/workspace_services/guacamole/guacamole-server/docker/Dockerfile b/templates/workspace_services/guacamole/guacamole-server/docker/Dockerfile
index f6089ef92a..c1ab1ca34a 100644
--- a/templates/workspace_services/guacamole/guacamole-server/docker/Dockerfile
+++ b/templates/workspace_services/guacamole/guacamole-server/docker/Dockerfile
@@ -11,9 +11,9 @@ RUN bash /tmp/maven_package_and_exit_succesfully.sh
 FROM scratch as test-results
 COPY --from=client_build /target/surefire-reports/* /
 
-FROM guacamole/guacd:1.5.2
+FROM guacamole/guacd:1.5.3
 
-ARG GUACAMOLE_AZURE_VERSION=0.3.3
+ARG GUACAMOLE_AZURE_VERSION=0.3.4
 
 ENV DEBIAN_FRONTEND=noninteractive
 
@@ -26,7 +26,7 @@ RUN apk add --update --no-cache wget openssh openjdk11-jre \
 
 ENV CATALINA_BASE=/usr/share/tomcat9/
 RUN TOMCAT_ARCHIVE="tomcat.tar.gz" && \
-    TOMCAT_VER="9.0.76" && \
+    TOMCAT_VER="9.0.83" && \
     wget -O "$TOMCAT_ARCHIVE" -N "https://archive.apache.org/dist/tomcat/tomcat-9/v${TOMCAT_VER}/bin/apache-tomcat-${TOMCAT_VER}.tar.gz" --progress=dot:giga && \
     tar xzf "$TOMCAT_ARCHIVE" && \
     rm -f "$TOMCAT_ARCHIVE" && \
@@ -53,7 +53,7 @@ COPY ./docker/services /etc/services.d/
 COPY --from=client_build /target/lib/* "${GUACAMOLE_LIB}"
 COPY --from=client_build "/target/guacamole-auth-tre-${GUACAMOLE_AZURE_VERSION}.jar" "${GUACAMOLE_HOME}/extensions/"
 
-RUN wget -O "${GUACAMOLE_HOME}/guacamole.war" "http://apache.org/dyn/closer.cgi?action=download&filename=guacamole/1.5.2/binary/guacamole-1.5.2.war" --progress=dot:giga
+RUN wget -O "${GUACAMOLE_HOME}/guacamole.war" "http://apache.org/dyn/closer.cgi?action=download&filename=guacamole/1.5.3/binary/guacamole-1.5.3.war" --progress=dot:giga
 
 ENV OAUTH2_PROXY_HOME=/etc/oauth2-proxy
 RUN OAUTH2_PROXY_ARCHIVE=oauth2-proxy.tar.gz && \
@@ -64,7 +64,7 @@ RUN OAUTH2_PROXY_ARCHIVE=oauth2-proxy.tar.gz && \
 
 COPY ./docker/index.jsp "$CATALINA_BASE"/webapps/ROOT/index.jsp
 
-RUN wget -O "/tmp/applicationinsights-agent.jar" "https://github.com/microsoft/ApplicationInsights-Java/releases/download/3.4.14/applicationinsights-agent-3.4.14.jar" --progress=dot:giga
+RUN wget -O "/tmp/applicationinsights-agent.jar" "https://github.com/microsoft/ApplicationInsights-Java/releases/download/3.4.18/applicationinsights-agent-3.4.18.jar" --progress=dot:giga
 ENV CATALINA_OPTS="$CATALINA_OPTS -javaagent:/tmp/applicationinsights-agent.jar"
 
 ENTRYPOINT [ "/init" ]
diff --git a/templates/workspace_services/guacamole/guacamole-server/docker/version.txt b/templates/workspace_services/guacamole/guacamole-server/docker/version.txt
index 777f190df0..8088f75131 100644
--- a/templates/workspace_services/guacamole/guacamole-server/docker/version.txt
+++ b/templates/workspace_services/guacamole/guacamole-server/docker/version.txt
@@ -1 +1 @@
-__version__ = "0.8.0"
+__version__ = "0.8.1"
diff --git a/templates/workspace_services/guacamole/guacamole-server/guacamole-auth-azure/pom.xml b/templates/workspace_services/guacamole/guacamole-server/guacamole-auth-azure/pom.xml
index 78ab4dec2d..c4572ea545 100644
--- a/templates/workspace_services/guacamole/guacamole-server/guacamole-auth-azure/pom.xml
+++ b/templates/workspace_services/guacamole/guacamole-server/guacamole-auth-azure/pom.xml
@@ -6,7 +6,7 @@
 
     <groupId>org.apache.guacamole</groupId>
     <artifactId>guacamole-auth-tre</artifactId>
-    <version>0.3.3</version>
+    <version>0.3.4</version>
     <packaging>jar</packaging>
     <name>guacamole-azure-tre</name>
 
@@ -41,7 +41,7 @@
         <dependency>
             <groupId>org.apache.guacamole</groupId>
             <artifactId>guacamole-ext</artifactId>
-            <version>1.5.2</version>
+            <version>1.5.3</version>
             <scope>provided</scope>
         </dependency>
         <!-- MS Azure dependencies -->
@@ -59,7 +59,7 @@
         <dependency>
             <groupId>org.json</groupId>
             <artifactId>json</artifactId>
-            <version>20230618</version>
+            <version>20231013</version>
         </dependency>
         <dependency>
             <groupId>org.apache.httpcomponents</groupId>
diff --git a/templates/workspace_services/guacamole/porter.yaml b/templates/workspace_services/guacamole/porter.yaml
index f58bafd202..18a50e9b83 100644
--- a/templates/workspace_services/guacamole/porter.yaml
+++ b/templates/workspace_services/guacamole/porter.yaml
@@ -1,7 +1,7 @@
 ---
 schemaVersion: 1.0.0
 name: tre-service-guacamole
-version: 0.10.5
+version: 0.10.6
 description: "An Azure TRE service for Guacamole"
 dockerfile: Dockerfile.tmpl
 registry: azuretre