diff --git a/chrome/browser/flag-metadata.json b/chrome/browser/flag-metadata.json
index 42567fce384ba0..400d760712e63f 100644
--- a/chrome/browser/flag-metadata.json
+++ b/chrome/browser/flag-metadata.json
@@ -830,7 +830,7 @@
   {
     "name": "contextual-search-force-caption",
     "owners": [ "//chrome/android/java/src/org/chromium/chrome/browser/contextualsearch/OWNERS", "contextual-search-eng@google.com" ],
-    "expiry_milestone": 95
+    "expiry_milestone": 99
   },
   {
     "name": "contextual-search-literal-search-tap",
@@ -840,7 +840,7 @@
   {
     "name": "contextual-search-longpress-resolve",
     "owners": [ "//chrome/android/java/src/org/chromium/chrome/browser/contextualsearch/OWNERS", "contextual-search-eng@google.com" ],
-    "expiry_milestone": 95
+    "expiry_milestone": 99
   },
   {
     "name": "contextual-search-ml-tap-suppression",
@@ -865,7 +865,7 @@
   {
     "name": "contextual-search-translations",
     "owners": [ "//chrome/android/java/src/org/chromium/chrome/browser/contextualsearch/OWNERS", "contextual-search-eng@google.com" ],
-    "expiry_milestone": 95
+    "expiry_milestone": 99
   },
   {
     "name": "contextual-search-twv-impl",
@@ -4588,27 +4588,27 @@
   {
     "name": "related-searches",
     "owners": [ "donnd", "related-searches-vteam@google.com" ],
-    "expiry_milestone": 97
+    "expiry_milestone": 99
   },
   {
     "name": "related-searches-alternate-ux",
     "owners": [ "donnd", "related-searches-vteam@google.com" ],
-    "expiry_milestone": 97
+    "expiry_milestone": 99
   },
   {
     "name": "related-searches-in-bar",
     "owners": [ "donnd", "related-searches-vteam@google.com" ],
-    "expiry_milestone": 97
+    "expiry_milestone": 99
   },
   {
     "name": "related-searches-simplified-ux",
     "owners": [ "donnd", "related-searches-vteam@google.com" ],
-    "expiry_milestone": 97
+    "expiry_milestone": 99
   },
   {
     "name": "related-searches-ui",
     "owners": [ "donnd", "related-searches-vteam@google.com" ],
-    "expiry_milestone": 97
+    "expiry_milestone": 99
   },
   {
     "name": "release-notes-notification-all-channels",
@@ -5006,7 +5006,7 @@
   {
     "name": "single-touch-select",
     "owners": [ "donnd", "contextual-search-eng@google.com" ],
-    "expiry_milestone": 97
+    "expiry_milestone": 99
   },
   {
     "_comment1": "Shipping some form of Site Isolation to Android is tracked",