diff --git a/website/assets/js/pages/device-management.page.js b/website/assets/js/pages/device-management.page.js
index 871b0e7db9..98a54c360f 100644
--- a/website/assets/js/pages/device-management.page.js
+++ b/website/assets/js/pages/device-management.page.js
@@ -40,6 +40,15 @@ parasails.registerPage('device-management-page', {
     closeModal: function() {
       this.modal = undefined;
     },
+    clickSwitchComparisonTableColumn: async function(option){
+      this.comparisonMode = option;
+      await setTimeout(()=>{
+        $('[data-toggle="tooltip"]').tooltip({
+          container: '#device-management-page',
+          trigger: 'hover',
+        });
+      }, 250);
+    },
     clickSwagRequestCTA: function () {
       if(window.gtag !== undefined){
         gtag('event','fleet_website__swag_request');
diff --git a/website/assets/js/pages/homepage.page.js b/website/assets/js/pages/homepage.page.js
index f71f58eef2..2456869326 100644
--- a/website/assets/js/pages/homepage.page.js
+++ b/website/assets/js/pages/homepage.page.js
@@ -124,6 +124,19 @@ parasails.registerPage('homepage', {
         });
       }, 250);
     },
+    clickSwitchComparisonTableColumn: async function(option){
+      if(this.comparisonTableMode === 'it'){
+        this.comparisonModeForIt = option;
+      } else {
+        this.comparisonModeForSecurity = option;
+      }
+      await setTimeout(()=>{
+        $('[data-toggle="tooltip"]').tooltip({
+          container: '#homepage',
+          trigger: 'hover',
+        });
+      }, 250);
+    },
     closeModal: function() {
       this.modal = undefined;
     },
diff --git a/website/assets/styles/pages/device-management.less b/website/assets/styles/pages/device-management.less
index e8684e3336..7452e9b247 100644
--- a/website/assets/styles/pages/device-management.less
+++ b/website/assets/styles/pages/device-management.less
@@ -184,6 +184,7 @@
       border: 1px solid @core-vibrant-blue-15;
       cursor: pointer;
       font-weight: 700;
+      white-space: nowrap;
     }
     [purpose='comparison-selector-dropwdown'] {
       width: 152px;
@@ -293,7 +294,18 @@
     font-weight: 700;
     color: #192147;
   }
-
+  [purpose='tooltip'] {
+    color: #515774;
+    font-size: 12px;
+    font-weight: 400;
+    line-height: 18px;
+    text-decoration-line: underline;
+    text-decoration-style: solid;
+    text-decoration-skip-ink: auto;
+    text-decoration-thickness: auto;
+    text-underline-offset: auto;
+    text-underline-position: from-font;
+  }
   [purpose='mobile-comparison-table'] {
     p {
       color: @core-fleet-black;
diff --git a/website/views/pages/device-management.ejs b/website/views/pages/device-management.ejs
index dcb6113792..8ed63d4a2f 100644
--- a/website/views/pages/device-management.ejs
+++ b/website/views/pages/device-management.ejs
@@ -122,18 +122,42 @@
                 {{comparisonModeFriendlyNames[comparisonMode]}}<img class="d-flex" style="width: 16px; height: 16px;" src="/images/chevron-down-16x16@2x.png" alt="a small shevron pointing downwards">
               </div>
               <div purpose="comparison-selector-dropwdown" class="dropdown-menu" aria-labelledby="dropdownMenuSelectPurpose">
-                <div class="dropdown-item" @click="comparisonMode = 'sccm'">SCCM</div>
-                <div class="dropdown-item" @click="comparisonMode = 'omnissa'">Omnissa (WS1)</div>
-                <div class="dropdown-item" @click="comparisonMode = 'jamf'">Jamf Pro</div>
-                <div class="dropdown-item" @click="comparisonMode = 'intune'">Intune</div>
-                <div class="dropdown-item" @click="comparisonMode = 'ansible'">Ansible</div>
-                <div class="dropdown-item" @click="comparisonMode = 'tanium'">Tanium</div>
-                <div class="dropdown-item" @click="comparisonMode = 'puppet'">Puppet</div>
-                <div class="dropdown-item" @click="comparisonMode = 'chef'">Chef</div>
+                <div class="dropdown-item" @click="clickSwitchComparisonTableColumn('sccm')">SCCM</div>
+                <div class="dropdown-item" @click="clickSwitchComparisonTableColumn('omnissa')">Omnissa (WS1)</div>
+                <div class="dropdown-item" @click="clickSwitchComparisonTableColumn('jamf')">Jamf Pro</div>
+                <div class="dropdown-item" @click="clickSwitchComparisonTableColumn('intune')">Intune</div>
+                <div class="dropdown-item" @click="clickSwitchComparisonTableColumn('ansible')">Ansible</div>
+                <div class="dropdown-item" @click="clickSwitchComparisonTableColumn('tanium')">Tanium</div>
+                <div class="dropdown-item" @click="clickSwitchComparisonTableColumn('puppet')">Puppet</div>
+                <div class="dropdown-item" @click="clickSwitchComparisonTableColumn('chef')">Chef</div>
               </div>
             </div>
           </div>
           <div purpose="comparison-table" class="d-sm-flex d-none flex-column">
+            <div purpose="table-row">
+              <div purpose="feature-name"><p>Cloud or self-host with no restrictions</p></div>
+              <div purpose="fleet-column">
+                <img class="mx-auto" alt="checkmark" purpose="checkmark" src="/images/icon-checkmark-green-16x16@2x.png">
+              </div>
+              <div purpose="comparison-column" v-if="comparisonMode === 'jamf'">
+                <p><a purpose="tooltip" data-toggle="tooltip" tabindex="0" data-placement="top" title="On-prem supported, but some key features, like Apple Declarative Device Management (DDM), are cloud-only.">On-prem limited</a></p>
+              </div>
+              <div purpose="comparison-column" v-else-if="comparisonMode === 'tanium'">
+                <p><a purpose="tooltip" data-toggle="tooltip" tabindex="0" data-placement="top" title="On-prem supported, but some modern modules and integrations are cloud-only.">On-prem limited</a></p>
+              </div>
+              <div purpose="comparison-column" v-else-if="comparisonMode === 'intune'">
+                <p>Cloud-only</p>
+              </div>
+              <div purpose="comparison-column" v-else-if="comparisonMode === 'sccm'">
+                <p>On-prem only</p>
+              </div>
+              <div purpose="comparison-column" v-else-if="comparisonMode === 'omnissa'">
+                <p>On-prem discouraged</p>
+              </div>
+              <div purpose="comparison-column" v-else>
+                <img class="mx-auto" alt="checkmark" purpose="checkmark" src="/images/icon-checkmark-green-16x16@2x.png">
+              </div>
+            </div>
             <div purpose="table-row">
               <div purpose="feature-name"><p>Zero-touch setup</p></div>
               <div purpose="fleet-column">
@@ -386,14 +410,44 @@
             {{comparisonModeFriendlyNames[comparisonMode]}}<img class="d-flex" style="width: 16px; height: 16px;" src="/images/chevron-down-16x16@2x.png" alt="a small shevron pointing downwards">
           </div>
           <div purpose="comparison-selector-dropwdown" class="dropdown-menu" aria-labelledby="mobileDropdownMenuSelectPurpose">
-              <div class="dropdown-item" @click="comparisonMode = 'sccm'">SCCM</div>
-              <div class="dropdown-item" @click="comparisonMode = 'omnissa'">Omnissa (WS1)</div>
-              <div class="dropdown-item" @click="comparisonMode = 'jamf'">Jamf Pro</div>
-              <div class="dropdown-item" @click="comparisonMode = 'intune'">Intune</div>
-              <div class="dropdown-item" @click="comparisonMode = 'ansible'">Ansible</div>
-              <div class="dropdown-item" @click="comparisonMode = 'tanium'">Tanium</div>
-              <div class="dropdown-item" @click="comparisonMode = 'puppet'">Puppet</div>
-              <div class="dropdown-item" @click="comparisonMode = 'chef'">Chef</div>
+            <div class="dropdown-item" @click="clickSwitchComparisonTableColumn('sccm')">SCCM</div>
+            <div class="dropdown-item" @click="clickSwitchComparisonTableColumn('omnissa')">Omnissa (WS1)</div>
+            <div class="dropdown-item" @click="clickSwitchComparisonTableColumn('jamf')">Jamf Pro</div>
+            <div class="dropdown-item" @click="clickSwitchComparisonTableColumn('intune')">Intune</div>
+            <div class="dropdown-item" @click="clickSwitchComparisonTableColumn('ansible')">Ansible</div>
+            <div class="dropdown-item" @click="clickSwitchComparisonTableColumn('tanium')">Tanium</div>
+            <div class="dropdown-item" @click="clickSwitchComparisonTableColumn('puppet')">Puppet</div>
+            <div class="dropdown-item" @click="clickSwitchComparisonTableColumn('chef')">Chef</div>
+          </div>
+          <div purpose="feature-table">
+            <div purpose="feature-name"><p>Cloud or self-host with no restrictions</p></div>
+            <div purpose="feature-table-row">
+              <div>Fleet</div>
+              <div purpose="feature-status">
+                <img class="mx-auto" alt="checkmark" purpose="checkmark" src="/images/icon-checkmark-green-16x16@2x.png">
+              </div>
+            </div>
+            <div purpose="feature-table-row">
+              <div>{{comparisonModeFriendlyNames[comparisonMode]}}</div>
+              <div purpose="feature-status" v-if="comparisonMode === 'jamf'">
+                <p><a purpose="tooltip" data-toggle="tooltip" tabindex="0" data-placement="top" title="On-prem supported, but some key features, like Apple Declarative Device Management (DDM), are cloud-only.">On-prem limited</a></p>
+              </div>
+              <div purpose="feature-status" v-else-if="comparisonMode === 'tanium'">
+                <p><a purpose="tooltip" data-toggle="tooltip" tabindex="0" data-placement="top" title="On-prem supported, but some modern modules and integrations are cloud-only.">On-prem limited</a></p>
+              </div>
+              <div purpose="feature-status" v-else-if="comparisonMode === 'intune'">
+                <p>Cloud-only</p>
+              </div>
+              <div purpose="feature-status" v-else-if="comparisonMode === 'sccm'">
+                <p>On-prem only</p>
+              </div>
+              <div purpose="feature-status" v-else-if="comparisonMode === 'omnissa'">
+                <p>On-prem discouraged</p>
+              </div>
+              <div purpose="feature-status" v-else>
+                <img class="mx-auto" alt="checkmark" purpose="checkmark" src="/images/icon-checkmark-green-16x16@2x.png">
+              </div>
+            </div>
           </div>
           <div purpose="feature-table">
             <div purpose="feature-name"><p>Zero-touch setup</p></div>
diff --git a/website/views/pages/homepage.ejs b/website/views/pages/homepage.ejs
index b71f5dfb59..5a633d71bb 100644
--- a/website/views/pages/homepage.ejs
+++ b/website/views/pages/homepage.ejs
@@ -182,18 +182,43 @@
                 {{comparisonModeFriendlyNames[comparisonModeForIt]}}<img class="d-flex" style="width: 16px; height: 16px;" src="/images/chevron-down-16x16@2x.png" alt="a small chevron pointing downwards">
               </div>
               <div purpose="comparison-selector-dropwdown" class="dropdown-menu" aria-labelledby="dropdownMenuSelectPurpose">
-                <div class="dropdown-item" @click="comparisonModeForIt = 'sccm'">SCCM</div>
-                <div class="dropdown-item" @click="comparisonModeForIt = 'omnissa'">Omnissa (WS1)</div>
-                <div class="dropdown-item" @click="comparisonModeForIt = 'jamf'">Jamf Pro</div>
-                <div class="dropdown-item" @click="comparisonModeForIt = 'intune'">Intune</div>
-                <div class="dropdown-item" @click="comparisonModeForIt = 'ansible'">Ansible</div>
-                <div class="dropdown-item" @click="comparisonModeForIt = 'tanium'">Tanium</div>
-                <div class="dropdown-item" @click="comparisonModeForIt = 'puppet'">Puppet</div>
-                <div class="dropdown-item" @click="comparisonModeForIt = 'chef'">Chef</div>
+                <div class="dropdown-item" @click="clickSwitchComparisonTableColumn('sccm')">SCCM</div>
+                <div class="dropdown-item" @click="clickSwitchComparisonTableColumn('omnissa')">Omnissa (WS1)</div>
+                <div class="dropdown-item" @click="clickSwitchComparisonTableColumn('jamf')">Jamf Pro</div>
+                <div class="dropdown-item" @click="clickSwitchComparisonTableColumn('intune')">Intune</div>
+                <div class="dropdown-item" @click="clickSwitchComparisonTableColumn('ansible')">Ansible</div>
+                <div class="dropdown-item" @click="clickSwitchComparisonTableColumn('tanium')">Tanium</div>
+                <div class="dropdown-item" @click="clickSwitchComparisonTableColumn('puppet')">Puppet</div>
+                <div class="dropdown-item" @click="clickSwitchComparisonTableColumn('chef')">Chef</div>
               </div>
             </div>
           </div>
           <div purpose="comparison-table" class="d-sm-flex d-none flex-column">
+            <div purpose="table-row">
+              <div purpose="feature-name"><p>Cloud or self-host with no restrictions</p></div>
+              <div purpose="fleet-column">
+                <img class="mx-auto" alt="checkmark" purpose="checkmark" src="/images/icon-checkmark-green-16x16@2x.png">
+              </div>
+              <div purpose="comparison-column" v-if="comparisonModeForIt === 'jamf'">
+                <p><a purpose="tooltip" data-toggle="tooltip" tabindex="0" data-placement="top" title="On-prem supported, but some key features, like Apple Declarative Device Management (DDM), are cloud-only.">On-prem limited</a></p>
+              </div>
+              <div purpose="comparison-column" v-else-if="comparisonModeForIt === 'tanium'">
+                <p><a purpose="tooltip" data-toggle="tooltip" tabindex="0" data-placement="top" title="On-prem supported, but some modern modules and integrations are cloud-only.">On-prem limited</a></p>
+              </div>
+              <div purpose="comparison-column" v-else-if="comparisonModeForIt === 'intune'">
+                <p>Cloud-only</p>
+              </div>
+              <div purpose="comparison-column" v-else-if="comparisonModeForIt === 'sccm'">
+                <p>On-prem only</p>
+              </div>
+              <div purpose="comparison-column" v-else-if="comparisonModeForIt === 'omnissa'">
+                <p>On-prem discouraged</p>
+              </div>
+              <div purpose="comparison-column" v-else>
+                <img class="mx-auto" alt="checkmark" purpose="checkmark" src="/images/icon-checkmark-green-16x16@2x.png">
+              </div>
+            </div>
+
             <div purpose="table-row">
               <div purpose="feature-name"><p>Zero-touch setup</p></div>
               <div purpose="fleet-column">
@@ -448,14 +473,45 @@
             {{comparisonModeFriendlyNames[comparisonModeForIt]}}<img class="d-flex" style="width: 16px; height: 16px;" src="/images/chevron-down-16x16@2x.png" alt="a small shevron pointing downwards">
           </div>
           <div purpose="comparison-selector-dropwdown" class="dropdown-menu" aria-labelledby="mobileDropdownMenuSelectPurpose">
-              <div class="dropdown-item" @click="comparisonModeForIt = 'sccm'">SCCM</div>
-              <div class="dropdown-item" @click="comparisonModeForIt = 'omnissa'">Omnissa (WS1)</div>
-              <div class="dropdown-item" @click="comparisonModeForIt = 'jamf'">Jamf Pro</div>
-              <div class="dropdown-item" @click="comparisonModeForIt = 'intune'">Intune</div>
-              <div class="dropdown-item" @click="comparisonModeForIt = 'ansible'">Ansible</div>
-              <div class="dropdown-item" @click="comparisonModeForIt = 'tanium'">Tanium</div>
-              <div class="dropdown-item" @click="comparisonModeForIt = 'puppet'">Puppet</div>
-              <div class="dropdown-item" @click="comparisonModeForIt = 'chef'">Chef</div>
+            <div class="dropdown-item" @click="clickSwitchComparisonTableColumn('sccm')">SCCM</div>
+            <div class="dropdown-item" @click="clickSwitchComparisonTableColumn('omnissa')">Omnissa (WS1)</div>
+            <div class="dropdown-item" @click="clickSwitchComparisonTableColumn('jamf')">Jamf Pro</div>
+            <div class="dropdown-item" @click="clickSwitchComparisonTableColumn('intune')">Intune</div>
+            <div class="dropdown-item" @click="clickSwitchComparisonTableColumn('ansible')">Ansible</div>
+            <div class="dropdown-item" @click="clickSwitchComparisonTableColumn('tanium')">Tanium</div>
+            <div class="dropdown-item" @click="clickSwitchComparisonTableColumn('puppet')">Puppet</div>
+            <div class="dropdown-item" @click="clickSwitchComparisonTableColumn('chef')">Chef</div>
+          </div>
+
+          <div purpose="feature-table">
+            <div purpose="feature-name"><p>Cloud or self-host with no restrictions</p></div>
+            <div purpose="feature-table-row">
+              <div>Fleet</div>
+              <div purpose="feature-status">
+                <img class="mx-auto" alt="checkmark" purpose="checkmark" src="/images/icon-checkmark-green-16x16@2x.png">
+              </div>
+            </div>
+            <div purpose="feature-table-row">
+              <div>{{comparisonModeFriendlyNames[comparisonModeForIt]}}</div>
+              <div purpose="feature-status" v-if="comparisonModeForIt === 'jamf'">
+                <p><a purpose="tooltip" data-toggle="tooltip" tabindex="0" data-placement="top" title="On-prem supported, but some key features, like Apple Declarative Device Management (DDM), are cloud-only.">On-prem limited</a></p>
+              </div>
+              <div purpose="feature-status" v-else-if="comparisonModeForIt === 'tanium'">
+                <p><a purpose="tooltip" data-toggle="tooltip" tabindex="0" data-placement="top" title="On-prem supported, but some modern modules and integrations are cloud-only.">On-prem limited</a></p>
+              </div>
+              <div purpose="feature-status" v-else-if="comparisonModeForIt === 'intune'">
+                <p>Cloud-only</p>
+              </div>
+              <div purpose="feature-status" v-else-if="comparisonModeForIt === 'sccm'">
+                <p>On-prem only</p>
+              </div>
+              <div purpose="feature-status" v-else-if="comparisonModeForIt === 'omnissa'">
+                <p>On-prem discouraged</p>
+              </div>
+              <div purpose="feature-status" v-else>
+                <img class="mx-auto" alt="checkmark" purpose="checkmark" src="/images/icon-checkmark-green-16x16@2x.png">
+              </div>
+            </div>
           </div>
           <div purpose="feature-table">
             <div purpose="feature-name"><p>Zero-touch setup</p></div>
@@ -784,12 +840,12 @@
                 {{comparisonModeFriendlyNames[comparisonModeForSecurity]}}<img class="d-flex" style="width: 16px; height: 16px;" src="/images/chevron-down-16x16@2x.png" alt="a small chevron pointing downwards">
               </div>
               <div purpose="comparison-selector-dropwdown" class="dropdown-menu" aria-labelledby="dropdownMenuSelectPurposeForSecurity">
-                <div class="dropdown-item" @click="comparisonModeForSecurity = 'defender'">Defender</div>
-                <div class="dropdown-item" @click="comparisonModeForSecurity = 'rapid'">Rapid 7</div>
-                <!-- <div class="dropdown-item" @click="comparisonModeForSecurity = 'crowdstrike'">Crowdstrike</div> -->
-                <div class="dropdown-item" @click="comparisonModeForSecurity = 'tanium'">Tanium</div>
-                <div class="dropdown-item" @click="comparisonModeForSecurity = 'qualys'">Qualys</div>
-                <div class="dropdown-item" @click="comparisonModeForSecurity = 'tenable'">Tenable</div>
+                <div class="dropdown-item" @click="clickSwitchComparisonTableColumn('defender')">Defender</div>
+                <div class="dropdown-item" @click="clickSwitchComparisonTableColumn('rapid')">Rapid 7</div>
+                <!-- <div class="dropdown-item" @click="clickSwitchComparisonTableColumn('crowdstrike')">Crowdstrike</div> -->
+                <div class="dropdown-item" @click="clickSwitchComparisonTableColumn('tanium')">Tanium</div>
+                <div class="dropdown-item" @click="clickSwitchComparisonTableColumn('qualys')">Qualys</div>
+                <div class="dropdown-item" @click="clickSwitchComparisonTableColumn('tenable')">Tenable</div>
               </div>
             </div>
           </div>
@@ -999,12 +1055,12 @@
             {{comparisonModeFriendlyNames[comparisonModeForSecurity]}}<img class="d-flex" style="width: 16px; height: 16px;" src="/images/chevron-down-16x16@2x.png" alt="a small shevron pointing downwards">
           </div>
           <div purpose="comparison-selector-dropwdown" class="dropdown-menu" aria-labelledby="mobileDropdownMenuSelectPurposeForSecurity">
-            <div class="dropdown-item" @click="comparisonModeForSecurity = 'rapid'">Rapid 7</div>
-            <div class="dropdown-item" @click="comparisonModeForSecurity = 'crowdstrike'">Crowdstrike</div>
-            <!-- <div class="dropdown-item" @click="comparisonModeForSecurity = 'defender'">Defender</div> -->
-            <div class="dropdown-item" @click="comparisonModeForSecurity = 'tanium'">Tanium</div>
-            <div class="dropdown-item" @click="comparisonModeForSecurity = 'qualys'">Qualys</div>
-            <div class="dropdown-item" @click="comparisonModeForSecurity = 'tenable'">Tenable</div>
+            <div class="dropdown-item" @click="clickSwitchComparisonTableColumn('defender')">Defender</div>
+            <div class="dropdown-item" @click="clickSwitchComparisonTableColumn('rapid')">Rapid 7</div>
+            <!-- <div class="dropdown-item" @click="clickSwitchComparisonTableColumn('crowdstrike')">Crowdstrike</div> -->
+            <div class="dropdown-item" @click="clickSwitchComparisonTableColumn('tanium')">Tanium</div>
+            <div class="dropdown-item" @click="clickSwitchComparisonTableColumn('qualys')">Qualys</div>
+            <div class="dropdown-item" @click="clickSwitchComparisonTableColumn('tenable')">Tenable</div>
           </div>
           <div purpose="feature-table">
             <div purpose="feature-name"><p>Threat intelligence <img style="margin-left: 6px;" class="d-inline" purpose="tooltip-icon" src="/images/icon-more-info-14x14@2x.png" alt="More info"  data-toggle="tooltip" tabindex="0" data-placement="top" title="Integrate threat intelligence sources to detect, enrich, or investigate suspicious activity on devices."></p></div>