diff --git a/CHANGELOG.md b/CHANGELOG.md
index db775061..99163978 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -9,6 +9,7 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 
 ### Fixed
 - Fixed spurious infinite loads with explore panel, file tree, and file search command. [#617](https://github.com/sourcebot-dev/sourcebot/pull/617)
+- Wipe search context on init if entitlement no longer exists [#618](https://github.com/sourcebot-dev/sourcebot/pull/618)
 
 ## [4.9.2] - 2025-11-13
 
diff --git a/packages/web/src/initialize.ts b/packages/web/src/initialize.ts
index fa27febd..97efc9ea 100644
--- a/packages/web/src/initialize.ts
+++ b/packages/web/src/initialize.ts
@@ -62,6 +62,18 @@ const initSingleTenancy = async () => {
         }
     }
 
+    // If we don't have the search context entitlement then wipe any existing
+    // search contexts that may be present in the DB. This could happen if a deployment had
+    // the entitlement, synced search contexts, and then no longer had the entitlement
+    const hasSearchContextEntitlement = hasEntitlement("search-contexts")
+    if(!hasSearchContextEntitlement) {
+        await prisma.searchContext.deleteMany({
+            where: {
+                orgId: SINGLE_TENANT_ORG_ID,
+            },
+        });
+    }
+
     // Sync anonymous access config from the config file
     const config = await loadConfig(env.CONFIG_PATH);
     const forceEnableAnonymousAccess = config.settings?.enablePublicAccess ?? env.FORCE_ENABLE_ANONYMOUS_ACCESS === 'true';