diff --git a/apps/web/app/(app)/[emailAccountId]/assistant/ResultDisplay.tsx b/apps/web/app/(app)/[emailAccountId]/assistant/ResultDisplay.tsx
index 7602e21f49..ee7fbae8e1 100644
--- a/apps/web/app/(app)/[emailAccountId]/assistant/ResultDisplay.tsx
+++ b/apps/web/app/(app)/[emailAccountId]/assistant/ResultDisplay.tsx
@@ -78,7 +78,10 @@ function ResultDisplay({
   }
 
   return (
-    <HoverCard content={<ResultDisplayContent result={result} />}>
+    <HoverCard
+      content={<ResultDisplayContent result={result} />}
+      className="w-80"
+    >
       <Badge color={rule ? "green" : "red"} className="whitespace-nowrap">
         {rule
           ? rule.name
@@ -136,7 +139,9 @@ export function ResultDisplayContent({ result }: { result: RunRulesResult }) {
                   type: action.type,
                   label: action.label,
                   folderName: action.folderName,
-                  content: action.content,
+                  content:
+                    action.content +
+                    "https://www.google.comasdjhgaghjdsghjasdgjasdjhasd",
                   to: action.to,
                   subject: action.subject,
                   cc: action.cc,
diff --git a/apps/web/components/HoverCard.tsx b/apps/web/components/HoverCard.tsx
index 0081254ca9..20458a305a 100644
--- a/apps/web/components/HoverCard.tsx
+++ b/apps/web/components/HoverCard.tsx
@@ -3,6 +3,7 @@ import {
   HoverCardContent,
   HoverCardTrigger,
 } from "@/components/ui/hover-card";
+import { cn } from "@/utils";
 
 export function HoverCard(props: {
   children: React.ReactNode;
@@ -12,7 +13,11 @@ export function HoverCard(props: {
   return (
     <HoverCardUi openDelay={100} closeDelay={100}>
       <HoverCardTrigger asChild>{props.children}</HoverCardTrigger>
-      <HoverCardContent className={props.className} align="start" side="right">
+      <HoverCardContent
+        className={cn("overflow-hidden", props.className)}
+        align="start"
+        side="right"
+      >
         {props.content}
       </HoverCardContent>
     </HoverCardUi>
diff --git a/apps/web/utils/ai/reply/reply-context-collector.ts b/apps/web/utils/ai/reply/reply-context-collector.ts
index 6798a74557..12fe0fd720 100644
--- a/apps/web/utils/ai/reply/reply-context-collector.ts
+++ b/apps/web/utils/ai/reply/reply-context-collector.ts
@@ -57,7 +57,7 @@ When searching, use natural language queries that would find relevant emails. Th
 Search Tips:
 - The search looks for EXACT text matches in emails
 - IMPORTANT: Try simpler queries if you don't get results for your first search
-- Try the subject line first if it contains the main topic
+- Do NOT use field prefixes like subject:, from:, to:, or label: - just use plain text queries
 
 Example search queries:
 - "order status" OR "shipment arrival" OR "tracking number"
diff --git a/apps/web/utils/email/microsoft.ts b/apps/web/utils/email/microsoft.ts
index ad31a0d911..d5cbe01e71 100644
--- a/apps/web/utils/email/microsoft.ts
+++ b/apps/web/utils/email/microsoft.ts
@@ -807,7 +807,11 @@ export class OutlookProvider implements EmailProvider {
 
     // For Outlook, separate search queries from date filters
     // Microsoft Graph API handles these differently
-    const originalQuery = options.query || "";
+    // Strip Gmail-style prefixes that don't work with Microsoft Graph
+    const originalQuery = (options.query || "").replace(
+      /\b(subject|label):/gi,
+      "",
+    );
 
     // Build date filter for Outlook (no quotes for DateTimeOffset comparison)
     const dateFilters: string[] = [];
diff --git a/apps/web/utils/logger.ts b/apps/web/utils/logger.ts
index 43d501dc28..df53bc595c 100644
--- a/apps/web/utils/logger.ts
+++ b/apps/web/utils/logger.ts
@@ -219,9 +219,13 @@ const REDACTED_FIELD_NAMES = new Set([
   "authorization",
 ]);
 
+// Fields containing email/message content - redacted in production unless debug logs enabled
+const CONTENT_FIELD_NAMES = new Set(["text", "body"]);
+
 /**
  * Recursively processes an object to protect sensitive data:
  * - REDACTED_FIELD_NAMES: Replaced with boolean (never logged)
+ * - CONTENT_FIELD_NAMES: Replaced with boolean in production (unless debug logs enabled)
  * - SENSITIVE_FIELD_NAMES: Hashed in production (raw in dev/test)
  *
  * Only works server-side - client-side logs are visible in browser anyway.
@@ -247,6 +251,10 @@ function hashSensitiveFields<T>(obj: T, depth = 0): T {
       if (REDACTED_FIELD_NAMES.has(key)) {
         processed[key] = !!value;
       }
+      // Redact content fields in production (unless debug logs enabled)
+      else if (CONTENT_FIELD_NAMES.has(key) && !env.ENABLE_DEBUG_LOGS) {
+        processed[key] = !!value;
+      }
       // Hash emails in production only (server-side only)
       else if (
         SENSITIVE_FIELD_NAMES.has(key) &&