diff --git a/repos/system_upgrade/el8toel9/actors/registerrubyirbadjustment/actor.py b/repos/system_upgrade/el8toel9/actors/registerrubyirbadjustment/actor.py
new file mode 100644
index 0000000000..ac4d1e6f66
--- /dev/null
+++ b/repos/system_upgrade/el8toel9/actors/registerrubyirbadjustment/actor.py
@@ -0,0 +1,22 @@
+from leapp.actors import Actor
+from leapp.models import DNFWorkaround
+from leapp.tags import FactsPhaseTag, IPUWorkflowTag
+
+
+class RegisterRubyIRBAdjustment(Actor):
+    """
+    Registers a workaround which will adjust the Ruby IRB directories during the upgrade.
+    """
+
+    name = 'register_ruby_irb_adjustment'
+    consumes = ()
+    produces = (DNFWorkaround,)
+    tags = (IPUWorkflowTag, FactsPhaseTag)
+
+    def process(self):
+        self.produce(
+            DNFWorkaround(
+                display_name='IRB directory fix',
+                script_path=self.get_tool_path('handlerubyirbsymlink'),
+            )
+        )
diff --git a/repos/system_upgrade/el8toel9/actors/registerrubyirbadjustment/tests/test_register_ruby_irb_adjustments.py b/repos/system_upgrade/el8toel9/actors/registerrubyirbadjustment/tests/test_register_ruby_irb_adjustments.py
new file mode 100644
index 0000000000..37dc833ec6
--- /dev/null
+++ b/repos/system_upgrade/el8toel9/actors/registerrubyirbadjustment/tests/test_register_ruby_irb_adjustments.py
@@ -0,0 +1,11 @@
+import os.path
+
+from leapp.models import DNFWorkaround
+
+
+def test_register_ruby_irb_adjustments(current_actor_context):
+    current_actor_context.run()
+    assert len(current_actor_context.consume(DNFWorkaround)) == 1
+    assert current_actor_context.consume(DNFWorkaround)[0].display_name == 'ruby irb symlink fix'
+    assert os.path.basename(current_actor_context.consume(DNFWorkaround)[0].script_path) == 'handlerubyirbsymlink'
+    assert os.path.exists(current_actor_context.consume(DNFWorkaround)[0].script_path)
diff --git a/repos/system_upgrade/el8toel9/tools/handlerubyirbsymlink b/repos/system_upgrade/el8toel9/tools/handlerubyirbsymlink
new file mode 100755
index 0000000000..9558dd486a
--- /dev/null
+++ b/repos/system_upgrade/el8toel9/tools/handlerubyirbsymlink
@@ -0,0 +1,23 @@
+#!/usr/bin/bash -e
+
+# just in case of hidden files.. not sure why would someone do that, it's more
+# like forgotten cache file possibility, but rather do that..
+shopt -s dotglob
+
+handle_dir() {
+    # Check that $1 is not already a symlink
+    # then remove the directory so that RPM can freely create the
+    # symlink.
+    if [ "$(readlink "$1")" == "/usr/share/gems/gems/irb-1.3.5" ]; then
+        return
+    fi
+
+    # There is no configuration or anything that the user should ever customize
+    # and expect to retain.
+    rm -rf "$1"
+
+    return 0
+}
+
+
+handle_dir /usr/share/ruby/irb