diff --git a/.changelog/14677.txt b/.changelog/14677.txt
new file mode 100644
index 000000000..e2b6438b2
--- /dev/null
+++ b/.changelog/14677.txt
@@ -0,0 +1,3 @@
+```release-note:improvement
+ui: attach timestamps and a visual indicator on failure to health checks in the Web UI
+```
diff --git a/ui/app/components/service-status-indicator.hbs b/ui/app/components/service-status-indicator.hbs
index 766c55481..66fe4c618 100644
--- a/ui/app/components/service-status-indicator.hbs
+++ b/ui/app/components/service-status-indicator.hbs
@@ -1 +1,10 @@
-<span class="service-status-indicator status-{{@check.Status}} tooltip is-right-aligned" aria-label="{{@check.Status}} at {{format-ts @check.Timestamp}}"></span>
+<span
+  class="service-status-indicator status-{{@check.Status}} tooltip is-right-aligned"
+  aria-label="{{@check.Status}} at {{format-ts @check.Timestamp}}"
+>
+  {{#if (eq @check.Status "failure")}}
+    &times;
+  {{/if}}
+
+  <span class="timestamp"><span>{{format-ts @check.Timestamp timeOnly=true}}</span></span>
+</span>
diff --git a/ui/app/helpers/format-ts.js b/ui/app/helpers/format-ts.js
index 1169efe0f..eab34613c 100644
--- a/ui/app/helpers/format-ts.js
+++ b/ui/app/helpers/format-ts.js
@@ -2,7 +2,11 @@ import moment from 'moment';
 import Helper from '@ember/component/helper';
 
 export function formatTs([date], options = {}) {
-  const format = options.short ? 'MMM D' : "MMM DD, 'YY HH:mm:ss ZZ";
+  const format = options.short
+    ? 'MMM D'
+    : options.timeOnly
+    ? 'HH:mm:ss'
+    : "MMM DD, 'YY HH:mm:ss ZZ";
   return moment(date).format(format);
 }
 
diff --git a/ui/app/styles/components/services.scss b/ui/app/styles/components/services.scss
index a2adc66e7..96d62365d 100644
--- a/ui/app/styles/components/services.scss
+++ b/ui/app/styles/components/services.scss
@@ -95,23 +95,77 @@ table.health-checks {
         width: calc(
           750px - 3rem - 50px
         ); //Sidebar width - padding - table padding
-        height: 20px;
+        height: 12px;
         padding-top: 30px;
         margin-top: -20px;
+        padding-bottom: 20px;
+        margin-bottom: -10px;
         overflow: hidden;
         box-sizing: content-box;
         .service-status-indicator {
-          width: 8px;
-          height: 8px;
+          width: 12px;
+          height: 12px;
           display: block;
           position: relative;
+          line-height: 10px;
+          text-align: center;
+          color: white;
+          border-radius: 2px;
           &.status-success {
             background-color: $nomad-green;
-            top: 0px;
           }
           &.status-failure {
             background-color: $red;
-            top: 12px;
+          }
+
+          & > .timestamp {
+            color: black;
+            font-size: 0.75rem;
+            position: absolute;
+            top: 100%;
+            text-align: center;
+            white-space: nowrap;
+            left: 50%;
+            width: 100px;
+            margin-left: -50px;
+            margin-top: calc(50% + 2px);
+
+            & > span {
+              visibility: hidden;
+            }
+
+            &:before {
+              display: none;
+              border-left: 1px solid $grey-blue;
+              content: '';
+              position: absolute;
+              left: 50%;
+              height: 50%;
+              top: -50%;
+            }
+
+            &:after {
+              display: block;
+              width: calc(12px + 2px); // account for grid.gap
+              border-top: 1px solid $grey-blue;
+              content: '';
+              position: absolute;
+              left: calc(50% - 1px);
+              margin-left: -6px;
+              top: calc(-50% - 1px);
+            }
+          }
+
+          &:nth-child(8n + 1) > .timestamp {
+            &:before {
+              display: block;
+            }
+            & > span {
+              visibility: visible;
+            }
+            & > span {
+              visibility: visible;
+            }
           }
         }
       }