diff --git a/website/assets/images/cta-thumbnail-psystage-5-feeling-confident-128x128@2x.png b/website/assets/images/cta-thumbnail-psystage-5-feeling-confident-128x128@2x.png
new file mode 100644
index 0000000000..e55f38deee
Binary files /dev/null and b/website/assets/images/cta-thumbnail-psystage-5-feeling-confident-128x128@2x.png differ
diff --git a/website/assets/images/psystage-5-feeling-confident-504x784@2x.png b/website/assets/images/psystage-5-feeling-confident-504x784@2x.png
new file mode 100644
index 0000000000..c74eebd6c9
Binary files /dev/null and b/website/assets/images/psystage-5-feeling-confident-504x784@2x.png differ
diff --git a/website/assets/images/psystage-6-has-team-buy-in-504x784@2x.png b/website/assets/images/psystage-6-has-team-buy-in-504x784@2x.png
index f601641ec4..fb0be98608 100644
Binary files a/website/assets/images/psystage-6-has-team-buy-in-504x784@2x.png and b/website/assets/images/psystage-6-has-team-buy-in-504x784@2x.png differ
diff --git a/website/assets/styles/layout.less b/website/assets/styles/layout.less
index 6eefec24a9..db13bd9d2c 100644
--- a/website/assets/styles/layout.less
+++ b/website/assets/styles/layout.less
@@ -160,7 +160,7 @@ html, body {
         background-image: url('/images/cta-thumbnail-psystage-4-has-use-case-128x128@2x.png');
       }
       &.stage-five {
-        background-image: url('/images/cta-thumbnail-psystage-5-100x100@2x.png');
+        background-image: url('/images/cta-thumbnail-psystage-5-feeling-confident-128x128@2x.png');
       }
       &.stage-six {
         background-image: url('/images/psystage-6-has-team-buy-in-504x784@2x.png');
diff --git a/website/assets/styles/pages/start.less b/website/assets/styles/pages/start.less
index 436d6fdb9d..70a7f24d33 100644
--- a/website/assets/styles/pages/start.less
+++ b/website/assets/styles/pages/start.less
@@ -82,7 +82,7 @@
       background-image: url('/images/psystage-4-has-use-case-508x784@2x.png');
     }
     &.stage-five {
-      background-image: url('/images/cropped-fleet-cloud-city-504x784@2x.png');
+      background-image: url('/images/psystage-5-feeling-confident-504x784@2x.png');
     }
     &.stage-six {
       background-image: url('/images/psystage-6-has-team-buy-in-504x784@2x.png');
diff --git a/website/views/pages/start.ejs b/website/views/pages/start.ejs
index 8326f87bf1..86c25b6c36 100644
--- a/website/views/pages/start.ejs
+++ b/website/views/pages/start.ejs
@@ -753,7 +753,7 @@
         </ajax-form>
       </div>
     </div>
-    <div purpose="form-image" :class="currentStep === 'start' ? 'stage-one' : ['thanks-for-checking-out-fleet', 'what-did-you-think'].includes(currentStep) ? 'cloud-city' : ['2 - Aware'].includes(psychologicalStage) ? 'stage-two' : ['3 - Intrigued'].includes(psychologicalStage) ? 'stage-three' : ['4 - Has use case'].includes(psychologicalStage) ? 'stage-four' : ['5 - Personally confident'].includes(psychologicalStage) ? 'stage-five' : ['6 - Has team buy-in'].includes(psychologicalStage) ? 'stage-six' : 'd-none w-0'">
+    <div purpose="form-image" :class="currentStep === 'start' ? 'stage-one' : ['thanks-for-checking-out-fleet'].includes(currentStep) ? 'cloud-city' : ['2 - Aware'].includes(psychologicalStage) ? 'stage-two' : ['3 - Intrigued'].includes(psychologicalStage) ? 'stage-three' : ['4 - Has use case'].includes(psychologicalStage) ? 'stage-four' : ['5 - Personally confident'].includes(psychologicalStage) ? 'stage-five' : ['6 - Has team buy-in'].includes(psychologicalStage) ? 'stage-six' : 'd-none w-0'">
     </div>
   </div>
 </div>