diff --git a/.github/workflows/fleet-and-orbit.yml b/.github/workflows/fleet-and-orbit.yml
index e1573239c1..bfcbd1ae97 100644
--- a/.github/workflows/fleet-and-orbit.yml
+++ b/.github/workflows/fleet-and-orbit.yml
@@ -340,6 +340,14 @@ jobs:
         with:
           name: fleet-osquery.pkg
 
+      - name: Wait until fleet address is reachable and fleet responds
+        run: |
+          until curl -v -fail ${{ needs.gen.outputs.address }}/version;
+          do
+            echo "Awaiting until fleet server responds..."
+            sleep 10
+          done
+
       - name: Install pkg
         run: |
           sudo hostname orbit-macos
@@ -391,6 +399,14 @@ jobs:
         with:
           name: fleet-osquery_42.0.0_amd64.deb
 
+      - name: Wait until fleet address is reachable and fleet responds
+        run: |
+          until curl -v -fail ${{ needs.gen.outputs.address }}/version;
+          do
+            echo "Awaiting until fleet server responds..."
+            sleep 10
+          done
+
       - name: Install deb
         run: |
           sudo hostname orbit-ubuntu
@@ -442,6 +458,14 @@ jobs:
         with:
           name: fleet-osquery.msi
 
+      - name: Wait until fleet address is reachable and fleet responds
+        run: |
+          until curl -v -fail ${{ needs.gen.outputs.address }}/version;
+          do
+            echo "Awaiting until fleet server responds..."
+            sleep 10
+          done
+
       - name: Install msi
         shell: pwsh
         run: |