diff --git a/rules/rules-reviewed/eap8/eap7/deprecated-initialcontextfactory-is-removed.windup.xml b/rules/rules-reviewed/eap8/eap7/deprecated-initialcontextfactory-is-removed.windup.xml
new file mode 100644
index 000000000..477bb58b7
--- /dev/null
+++ b/rules/rules-reviewed/eap8/eap7/deprecated-initialcontextfactory-is-removed.windup.xml
@@ -0,0 +1,33 @@
+<?xml version="1.0"?>
+<ruleset xmlns="http://windup.jboss.org/schema/jboss-ruleset" id="deprecated-initialcontextfactory-is-removed"
+         xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance"
+         xsi:schemaLocation="http://windup.jboss.org/schema/jboss-ruleset http://windup.jboss.org/schema/jboss-ruleset/windup-jboss-ruleset.xsd">
+    <metadata>
+        <description>
+            This ruleset provides analysis of Java EE applications that need to change their sources due to the removal of deprecated InitialContextFactory class.
+        </description>
+        <dependencies>
+            <addon id="org.jboss.windup.rules,windup-rules-javaee,3.0.0.Final" />
+            <addon id="org.jboss.windup.rules,windup-rules-java,3.0.0.Final" />
+            <addon id="org.jboss.windup.rules,windup-rules-xml,3.0.0.Final" />
+        </dependencies>
+        <sourceTechnology id="eap" versionRange="[6,8)" />
+        <targetTechnology id="eap" versionRange="[8,)" />
+    </metadata>
+    <rules>
+        <rule id="deprecated-initialcontextfactory-is-removed-00001">
+            <when>
+                <or>
+                    <javaclass references="org.jboss.naming.remote.client.InitialContextFactory" />
+                    <filecontent pattern="org.jboss.naming.remote.client.InitialContextFactory" filename="{*}.wsdl"/>
+                </or>
+            </when>
+            <perform>
+                <hint title="Class org.jboss.naming.remote.client.InitialContextFactory has been removed" effort="1" category-id="mandatory">
+                    <message>Replace this class with `org.wildfly.naming.client.WildFlyInitialContextFactory`.</message>
+                    <tag>JakartaEE</tag>
+                </hint>
+            </perform>
+        </rule>
+    </rules>
+</ruleset>
diff --git a/rules/rules-reviewed/eap8/eap7/tests/data/deprecated-initialcontextfactory-is-removed/DeprecatedInitialcontextfactoryIsRemoved.java b/rules/rules-reviewed/eap8/eap7/tests/data/deprecated-initialcontextfactory-is-removed/DeprecatedInitialcontextfactoryIsRemoved.java
new file mode 100644
index 000000000..444b0b359
--- /dev/null
+++ b/rules/rules-reviewed/eap8/eap7/tests/data/deprecated-initialcontextfactory-is-removed/DeprecatedInitialcontextfactoryIsRemoved.java
@@ -0,0 +1,10 @@
+import org.jboss.naming.remote.client.InitialContextFactory;
+
+public class DeprecatedInitialcontextfactoryIsRemoved {
+
+    String propertyValue = "org.jboss.naming.remote.client.InitialContextFactory";
+    
+    public String getDeprecatedClassName() {
+        return InitialContextFactory.class.getName();
+    }
+}
\ No newline at end of file
diff --git a/rules/rules-reviewed/eap8/eap7/tests/data/deprecated-initialcontextfactory-is-removed/deprecated-initialcontextfactory-is-removed.wsdl b/rules/rules-reviewed/eap8/eap7/tests/data/deprecated-initialcontextfactory-is-removed/deprecated-initialcontextfactory-is-removed.wsdl
new file mode 100644
index 000000000..73abc0a67
--- /dev/null
+++ b/rules/rules-reviewed/eap8/eap7/tests/data/deprecated-initialcontextfactory-is-removed/deprecated-initialcontextfactory-is-removed.wsdl
@@ -0,0 +1,8 @@
+<definitions name = "HelloService"
+             targetNamespace = "http://www.examples.com/wsdl/HelloService.wsdl"
+             xmlns = "http://schemas.xmlsoap.org/wsdl/"
+             xmlns:soapjms = "http://schemas.xmlsoap.org/wsdl/soap/">
+    <service name="exampleService">
+        <soapjms:jndiInitialContextFactory>org.jboss.naming.remote.client.InitialContextFactory</soapjms:jndiInitialContextFactory>
+    </service>
+</definitions>    
\ No newline at end of file
diff --git a/rules/rules-reviewed/eap8/eap7/tests/deprecated-initialcontextfactory-is-removed.windup.test.xml b/rules/rules-reviewed/eap8/eap7/tests/deprecated-initialcontextfactory-is-removed.windup.test.xml
new file mode 100644
index 000000000..a404a41c2
--- /dev/null
+++ b/rules/rules-reviewed/eap8/eap7/tests/deprecated-initialcontextfactory-is-removed.windup.test.xml
@@ -0,0 +1,36 @@
+<?xml version="1.0"?>
+<ruletest id="deprecated-initialcontextfactory-is-removed-tests"
+          xmlns="http://windup.jboss.org/schema/jboss-ruleset"
+          xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance"
+          xsi:schemaLocation="http://windup.jboss.org/schema/jboss-ruleset http://windup.jboss.org/schema/jboss-ruleset/windup-jboss-ruleset.xsd">
+    <testDataPath>data/deprecated-initialcontextfactory-is-removed</testDataPath>
+    <rulePath>../deprecated-initialcontextfactory-is-removed.windup.xml</rulePath>
+    <ruleset>
+        <rules>
+            <rule id="deprecated-initialcontextfactory-is-removed-00001-test">
+                <when>
+                    <not>
+                        <iterable-filter size="3">
+                            <hint-exists message="Replace this class with `org.wildfly.naming.client.WildFlyInitialContextFactory`."/>
+                        </iterable-filter>
+                    </not>
+                </when>
+                <perform>
+                    <fail message="[deprecated-initialcontextfactory-is-removed-00001] The hint was not found!" />
+                </perform>
+            </rule>
+            <rule id="picketlink-00020-test">
+                <when>
+                    <not>
+                        <iterable-filter size="1">
+                            <hint-exists message="Configure an RH-SSO SAML client and then generate a keycloak-saml.xml file using the RH-SSO admin console. Add the keycloak-saml.xml file to the deployment’s WEB-INF directory. Set the auth-method to KEYCLOAK-SAML in the deployment’s web.xml file."/>
+                        </iterable-filter>
+                    </not>
+                </when>
+                <perform>
+                    <fail message="[picketlink-00020] The hint was not found!" />
+                </perform>
+            </rule>
+        </rules>
+    </ruleset>
+</ruletest>
\ No newline at end of file