diff --git a/server/private/license/license.ts b/server/private/license/license.ts
index 61ea23b48..0ff77bc4f 100644
--- a/server/private/license/license.ts
+++ b/server/private/license/license.ts
@@ -50,6 +50,27 @@ type ValidateLicenseAPIResponse = {
     status: number;
 };
 
+// Ranks license tiers so that when multiple license keys are active, the
+// highest tier among them wins. Order: personal < tier1 < tier2 < ... <
+// tier[n] < enterprise. Tier numbers are parsed so this scales to any
+// tier[n] without needing updates here.
+function tierRank(tier?: LicenseKeyTier): number {
+    if (!tier) {
+        return -1;
+    }
+    if (tier === "enterprise") {
+        return Number.MAX_SAFE_INTEGER;
+    }
+    if (tier === "personal") {
+        return 0;
+    }
+    const match = /^tier(\d+)$/.exec(tier);
+    if (match) {
+        return parseInt(match[1], 10);
+    }
+    return 0;
+}
+
 type TokenPayload = {
     valid: boolean;
     type: LicenseKeyType;
@@ -371,12 +392,22 @@ LQIDAQAB
             }
 
             // Compute host status: quantity = users, quantity_2 = sites
+            // When multiple host keys are active, prefer a valid key over an
+            // invalid one, and among equally-valid keys prefer the highest tier.
+            let selectedHostKey: LicenseKeyCache | undefined;
             for (const key of keys) {
                 const cached = newCache.get(key.licenseKey)!;
 
                 if (cached.type === "host") {
-                    status.isLicenseValid = cached.valid;
-                    status.tier = cached.tier;
+                    if (
+                        !selectedHostKey ||
+                        (cached.valid && !selectedHostKey.valid) ||
+                        (cached.valid === selectedHostKey.valid &&
+                            tierRank(cached.tier) >
+                                tierRank(selectedHostKey.tier))
+                    ) {
+                        selectedHostKey = cached;
+                    }
                 }
 
                 if (!cached.valid) {
@@ -393,6 +424,11 @@ LQIDAQAB
                 }
             }
 
+            if (selectedHostKey) {
+                status.isLicenseValid = selectedHostKey.valid;
+                status.tier = selectedHostKey.tier;
+            }
+
             // Invalidate license if over user or site limits
             if (
                 (status.maxSites !== undefined &&