Add better search management and operators + contact search quick link

app/repository/messages.py

@@ -1,5 +1,7 @@
 import json
+import re
 import time
+from dataclasses import dataclass
 from typing import Any
 
 from app.database import db
@@ -12,6 +14,17 @@ from app.models import (
 
 
 class MessageRepository:
+    @dataclass
+    class _SearchQuery:
+        free_text: str
+        user_terms: list[str]
+        channel_terms: list[str]
+
+    _SEARCH_OPERATOR_RE = re.compile(
+        r'(?<!\S)(user|channel):(?:"((?:[^"\\]|\\.)*)"|(\S+))',
+        re.IGNORECASE,
+    )
+
     @staticmethod
     def _contact_activity_filter(public_key: str) -> tuple[str, list[Any]]:
         lower_key = public_key.lower()
@@ -185,6 +198,92 @@ class MessageRepository:
         else:
             return "AND conversation_key LIKE ?", f"{conversation_key}%"
 
+    @staticmethod
+    def _unescape_search_quoted_value(value: str) -> str:
+        return value.replace('\\"', '"').replace("\\\\", "\\")
+
+    @staticmethod
+    def _parse_search_query(q: str) -> _SearchQuery:
+        user_terms: list[str] = []
+        channel_terms: list[str] = []
+        fragments: list[str] = []
+        last_end = 0
+
+        for match in MessageRepository._SEARCH_OPERATOR_RE.finditer(q):
+            fragments.append(q[last_end : match.start()])
+            raw_value = match.group(2) if match.group(2) is not None else match.group(3) or ""
+            value = MessageRepository._unescape_search_quoted_value(raw_value)
+            if match.group(1).lower() == "user":
+                user_terms.append(value)
+            else:
+                channel_terms.append(value)
+            last_end = match.end()
+
+        if not user_terms and not channel_terms:
+            return MessageRepository._SearchQuery(free_text=q, user_terms=[], channel_terms=[])
+
+        fragments.append(q[last_end:])
+        free_text = " ".join(fragment.strip() for fragment in fragments if fragment.strip())
+        return MessageRepository._SearchQuery(
+            free_text=free_text,
+            user_terms=user_terms,
+            channel_terms=channel_terms,
+        )
+
+    @staticmethod
+    def _escape_like(value: str) -> str:
+        return value.replace("\\", "\\\\").replace("%", "\\%").replace("_", "\\_")
+
+    @staticmethod
+    def _looks_like_hex_prefix(value: str) -> bool:
+        return bool(value) and all(ch in "0123456789abcdefABCDEF" for ch in value)
+
+    @staticmethod
+    def _build_channel_scope_clause(value: str) -> tuple[str, list[Any]]:
+        params: list[Any] = [value]
+        clause = "(messages.type = 'CHAN' AND (channels.name = ? COLLATE NOCASE"
+
+        if MessageRepository._looks_like_hex_prefix(value):
+            if len(value) == 32:
+                clause += " OR UPPER(messages.conversation_key) = ?"
+                params.append(value.upper())
+            else:
+                clause += " OR UPPER(messages.conversation_key) LIKE ? ESCAPE '\\'"
+                params.append(f"{MessageRepository._escape_like(value.upper())}%")
+
+        clause += "))"
+        return clause, params
+
+    @staticmethod
+    def _build_user_scope_clause(value: str) -> tuple[str, list[Any]]:
+        params: list[Any] = [value, value]
+        clause = (
+            "((messages.type = 'PRIV' AND contacts.name = ? COLLATE NOCASE)"
+            " OR (messages.type = 'CHAN' AND sender_name = ? COLLATE NOCASE)"
+        )
+
+        if MessageRepository._looks_like_hex_prefix(value):
+            lower_value = value.lower()
+            priv_key_clause: str
+            chan_key_clause: str
+            if len(value) == 64:
+                priv_key_clause = "LOWER(messages.conversation_key) = ?"
+                chan_key_clause = "LOWER(sender_key) = ?"
+                params.extend([lower_value, lower_value])
+            else:
+                escaped_prefix = f"{MessageRepository._escape_like(lower_value)}%"
+                priv_key_clause = "LOWER(messages.conversation_key) LIKE ? ESCAPE '\\'"
+                chan_key_clause = "LOWER(sender_key) LIKE ? ESCAPE '\\'"
+                params.extend([escaped_prefix, escaped_prefix])
+
+            clause += (
+                f" OR (messages.type = 'PRIV' AND {priv_key_clause})"
+                f" OR (messages.type = 'CHAN' AND sender_key IS NOT NULL AND {chan_key_clause})"
+            )
+
+        clause += ")"
+        return clause, params
+
     @staticmethod
     def _row_to_message(row: Any) -> Message:
         """Convert a database row to a Message model."""
@@ -218,15 +317,24 @@ class MessageRepository:
         blocked_keys: list[str] | None = None,
         blocked_names: list[str] | None = None,
     ) -> list[Message]:
-        query = "SELECT * FROM messages WHERE 1=1"
+        search_query = MessageRepository._parse_search_query(q) if q else None
+        query = (
+            "SELECT messages.* FROM messages "
+            "LEFT JOIN contacts ON messages.type = 'PRIV' "
+            "AND LOWER(messages.conversation_key) = LOWER(contacts.public_key) "
+            "LEFT JOIN channels ON messages.type = 'CHAN' "
+            "AND UPPER(messages.conversation_key) = UPPER(channels.key) "
+            "WHERE 1=1"
+        )
         params: list[Any] = []
 
         if blocked_keys:
             placeholders = ",".join("?" for _ in blocked_keys)
             query += (
-                f" AND NOT (outgoing=0 AND ("
-                f"(type='PRIV' AND LOWER(conversation_key) IN ({placeholders}))"
-                f" OR (type='CHAN' AND sender_key IS NOT NULL AND LOWER(sender_key) IN ({placeholders}))"
+                f" AND NOT (messages.outgoing=0 AND ("
+                f"(messages.type='PRIV' AND LOWER(messages.conversation_key) IN ({placeholders}))"
+                f" OR (messages.type='CHAN' AND messages.sender_key IS NOT NULL"
+                f" AND LOWER(messages.sender_key) IN ({placeholders}))"
                 f"))"
             )
             params.extend(blocked_keys)
@@ -235,36 +343,57 @@ class MessageRepository:
         if blocked_names:
             placeholders = ",".join("?" for _ in blocked_names)
             query += (
-                f" AND NOT (outgoing=0 AND sender_name IS NOT NULL"
-                f" AND sender_name IN ({placeholders}))"
+                f" AND NOT (messages.outgoing=0 AND messages.sender_name IS NOT NULL"
+                f" AND messages.sender_name IN ({placeholders}))"
             )
             params.extend(blocked_names)
 
         if msg_type:
-            query += " AND type = ?"
+            query += " AND messages.type = ?"
             params.append(msg_type)
         if conversation_key:
             clause, norm_key = MessageRepository._normalize_conversation_key(conversation_key)
-            query += f" {clause}"
+            query += f" {clause.replace('conversation_key', 'messages.conversation_key')}"
             params.append(norm_key)
 
-        if q:
-            escaped_q = q.replace("\\", "\\\\").replace("%", "\\%").replace("_", "\\_")
-            query += " AND text LIKE ? ESCAPE '\\' COLLATE NOCASE"
+        if search_query and search_query.user_terms:
+            scope_clauses: list[str] = []
+            for term in search_query.user_terms:
+                clause, clause_params = MessageRepository._build_user_scope_clause(term)
+                scope_clauses.append(clause)
+                params.extend(clause_params)
+            query += f" AND ({' OR '.join(scope_clauses)})"
+
+        if search_query and search_query.channel_terms:
+            scope_clauses = []
+            for term in search_query.channel_terms:
+                clause, clause_params = MessageRepository._build_channel_scope_clause(term)
+                scope_clauses.append(clause)
+                params.extend(clause_params)
+            query += f" AND ({' OR '.join(scope_clauses)})"
+
+        if search_query and search_query.free_text:
+            escaped_q = MessageRepository._escape_like(search_query.free_text)
+            query += " AND messages.text LIKE ? ESCAPE '\\' COLLATE NOCASE"
             params.append(f"%{escaped_q}%")
 
         # Forward cursor (after/after_id) — mutually exclusive with before/before_id
         if after is not None and after_id is not None:
-            query += " AND (received_at > ? OR (received_at = ? AND id > ?))"
+            query += (
+                " AND (messages.received_at > ? OR (messages.received_at = ? AND messages.id > ?))"
+            )
             params.extend([after, after, after_id])
-            query += " ORDER BY received_at ASC, id ASC LIMIT ?"
+            query += " ORDER BY messages.received_at ASC, messages.id ASC LIMIT ?"
             params.append(limit)
         else:
             if before is not None and before_id is not None:
-                query += " AND (received_at < ? OR (received_at = ? AND id < ?))"
+                query += (
+                    " AND (messages.received_at < ?"
+                    " OR (messages.received_at = ? AND messages.id < ?))"
+                )
                 params.extend([before, before, before_id])
 
-            query += " ORDER BY received_at DESC, id DESC LIMIT ?"
+            query += " ORDER BY messages.received_at DESC, messages.id DESC LIMIT ?"
             params.append(limit)
             if before is None or before_id is None:
                 query += " OFFSET ?"

frontend/src/App.tsx

@@ -21,6 +21,10 @@ import { messageContainsMention } from './utils/messageParser';
 import type { Conversation, RawPacket } from './types';
 
 export function App() {
+  const quoteSearchOperatorValue = useCallback((value: string) => {
+    return `"${value.replace(/\\/g, '\\\\').replace(/"/g, '\\"')}"`;
+  }, []);
+
   const messageInputRef = useRef<MessageInputHandle>(null);
   const [rawPackets, setRawPackets] = useState<RawPacket[]>([]);
   const {
@@ -150,6 +154,7 @@ export function App() {
     infoPaneContactKey,
     infoPaneFromChannel,
     infoPaneChannelKey,
+    searchPrefillRequest,
     handleOpenContactInfo,
     handleCloseContactInfo,
     handleOpenChannelInfo,
@@ -157,6 +162,7 @@ export function App() {
     handleSelectConversationWithTargetReset,
     handleNavigateToChannel,
     handleNavigateToMessage,
+    handleOpenSearchWithQuery,
   } = useConversationNavigation({
     channels,
     handleSelectConversation,
@@ -322,6 +328,7 @@ export function App() {
     contacts,
     channels,
     onNavigateToMessage: handleNavigateToMessage,
+    prefillRequest: searchPrefillRequest,
   };
   const settingsProps = {
     config,
@@ -361,6 +368,12 @@ export function App() {
     favorites,
     onToggleFavorite: handleToggleFavorite,
     onNavigateToChannel: handleNavigateToChannel,
+    onSearchMessagesByKey: (publicKey: string) => {
+      handleOpenSearchWithQuery(`user:${publicKey}`);
+    },
+    onSearchMessagesByName: (name: string) => {
+      handleOpenSearchWithQuery(`user:${quoteSearchOperatorValue(name)}`);
+    },
     onToggleBlockedKey: handleBlockKey,
     onToggleBlockedName: handleBlockName,
     blockedKeys: appSettings?.blocked_keys ?? [],

frontend/src/components/ContactInfoPane.tsx

@@ -1,5 +1,5 @@
 import { type ReactNode, useEffect, useState } from 'react';
-import { Ban, Star } from 'lucide-react';
+import { Ban, Search, Star } from 'lucide-react';
 import { api } from '../api';
 import { formatTime } from '../utils/messageParser';
 import {
@@ -51,6 +51,8 @@ interface ContactInfoPaneProps {
   favorites: Favorite[];
   onToggleFavorite: (type: 'channel' | 'contact', id: string) => void;
   onNavigateToChannel?: (channelKey: string) => void;
+  onSearchMessagesByKey?: (publicKey: string) => void;
+  onSearchMessagesByName?: (name: string) => void;
   blockedKeys?: string[];
   blockedNames?: string[];
   onToggleBlockedKey?: (key: string) => void;
@@ -66,6 +68,8 @@ export function ContactInfoPane({
   favorites,
   onToggleFavorite,
   onNavigateToChannel,
+  onSearchMessagesByKey,
+  onSearchMessagesByName,
   blockedKeys = [],
   blockedNames = [],
   onToggleBlockedKey,
@@ -183,6 +187,19 @@ export function ContactInfoPane({
               </div>
             )}
 
+            {onSearchMessagesByName && (
+              <div className="px-5 py-3 border-b border-border">
+                <button
+                  type="button"
+                  className="text-sm flex items-center gap-2 hover:text-primary transition-colors"
+                  onClick={() => onSearchMessagesByName(nameOnlyValue)}
+                >
+                  <Search className="h-4.5 w-4.5 text-muted-foreground" aria-hidden="true" />
+                  <span>Search user&apos;s messages by name</span>
+                </button>
+              </div>
+            )}
+
             {fromChannel && (
               <ChannelAttributionWarning
                 nameOnly
@@ -387,6 +404,19 @@ export function ContactInfoPane({
               </div>
             )}
 
+            {onSearchMessagesByKey && (
+              <div className="px-5 py-3 border-b border-border">
+                <button
+                  type="button"
+                  className="text-sm flex items-center gap-2 hover:text-primary transition-colors"
+                  onClick={() => onSearchMessagesByKey(contact.public_key)}
+                >
+                  <Search className="h-4.5 w-4.5 text-muted-foreground" aria-hidden="true" />
+                  <span>Search user&apos;s messages by key</span>
+                </button>
+              </div>
+            )}
+
             {/* Nearest Repeaters */}
             {analytics && analytics.nearest_repeaters.length > 0 && (
               <div className="px-5 py-3 border-b border-border">

frontend/src/components/SearchView.tsx

@@ -19,6 +19,8 @@ interface SearchResult {
   sender_name: string | null;
 }
 
+const SEARCH_OPERATOR_RE = /(?<!\S)(user|channel):(?:"((?:[^"\\]|\\.)*)"|(\S+))/gi;
+
 export interface SearchNavigateTarget {
   id: number;
   type: 'PRIV' | 'CHAN';
@@ -30,6 +32,10 @@ export interface SearchViewProps {
   contacts: Contact[];
   channels: Channel[];
   onNavigateToMessage: (target: SearchNavigateTarget) => void;
+  prefillRequest?: {
+    query: string;
+    nonce: number;
+  } | null;
 }
 
 function highlightMatch(text: string, query: string): React.ReactNode[] {
@@ -53,7 +59,34 @@ function highlightMatch(text: string, query: string): React.ReactNode[] {
   return parts;
 }
 
-export function SearchView({ contacts, channels, onNavigateToMessage }: SearchViewProps) {
+function getHighlightQuery(query: string): string {
+  const fragments: string[] = [];
+  let lastIndex = 0;
+  let foundOperator = false;
+
+  for (const match of query.matchAll(SEARCH_OPERATOR_RE)) {
+    foundOperator = true;
+    fragments.push(query.slice(lastIndex, match.index));
+    lastIndex = (match.index ?? 0) + match[0].length;
+  }
+
+  if (!foundOperator) {
+    return query;
+  }
+
+  fragments.push(query.slice(lastIndex));
+  return fragments
+    .map((fragment) => fragment.trim())
+    .filter(Boolean)
+    .join(' ');
+}
+
+export function SearchView({
+  contacts,
+  channels,
+  onNavigateToMessage,
+  prefillRequest = null,
+}: SearchViewProps) {
   const [query, setQuery] = useState('');
   const [debouncedQuery, setDebouncedQuery] = useState('');
   const [results, setResults] = useState<SearchResult[]>([]);
@@ -62,6 +95,7 @@ export function SearchView({ contacts, channels, onNavigateToMessage }: SearchVi
   const [offset, setOffset] = useState(0);
   const abortRef = useRef<AbortController | null>(null);
   const inputRef = useRef<HTMLInputElement>(null);
+  const highlightQuery = getHighlightQuery(debouncedQuery);
 
   // Debounce query
   useEffect(() => {
@@ -78,6 +112,17 @@ export function SearchView({ contacts, channels, onNavigateToMessage }: SearchVi
     setHasMore(false);
   }, [debouncedQuery]);
 
+  useEffect(() => {
+    if (!prefillRequest) {
+      return;
+    }
+
+    const nextQuery = prefillRequest.query.trim();
+    setQuery(nextQuery);
+    setDebouncedQuery(nextQuery);
+    inputRef.current?.focus();
+  }, [prefillRequest]);
+
   // Fetch search results
   useEffect(() => {
     if (!debouncedQuery) {
@@ -193,7 +238,11 @@ export function SearchView({ contacts, channels, onNavigateToMessage }: SearchVi
       <div className="flex-1 overflow-y-auto">
         {!debouncedQuery && (
           <div className="p-8 text-center text-muted-foreground text-sm">
-            Type to search across all messages
+            <p>Type to search across all messages</p>
+            <p className="mt-2 text-xs">
+              Tip: use <code>user:</code> or <code>channel:</code> for keys or names, and wrap names
+              with spaces in them in quotes.
+            </p>
           </div>
         )}
 
@@ -246,7 +295,7 @@ export function SearchView({ contacts, channels, onNavigateToMessage }: SearchVi
                   result.sender_name && result.text.startsWith(`${result.sender_name}: `)
                     ? result.text.slice(result.sender_name.length + 2)
                     : result.text,
-                  debouncedQuery
+                  highlightQuery
                 )}
               </div>
             </div>

frontend/src/hooks/useConversationNavigation.ts

@@ -14,6 +14,7 @@ interface UseConversationNavigationResult {
   infoPaneContactKey: string | null;
   infoPaneFromChannel: boolean;
   infoPaneChannelKey: string | null;
+  searchPrefillRequest: { query: string; nonce: number } | null;
   handleOpenContactInfo: (publicKey: string, fromChannel?: boolean) => void;
   handleCloseContactInfo: () => void;
   handleOpenChannelInfo: (channelKey: string) => void;
@@ -24,6 +25,7 @@ interface UseConversationNavigationResult {
   ) => void;
   handleNavigateToChannel: (channelKey: string) => void;
   handleNavigateToMessage: (target: SearchNavigateTarget) => void;
+  handleOpenSearchWithQuery: (query: string) => void;
 }
 
 export function useConversationNavigation({
@@ -34,6 +36,10 @@ export function useConversationNavigation({
   const [infoPaneContactKey, setInfoPaneContactKey] = useState<string | null>(null);
   const [infoPaneFromChannel, setInfoPaneFromChannel] = useState(false);
   const [infoPaneChannelKey, setInfoPaneChannelKey] = useState<string | null>(null);
+  const [searchPrefillRequest, setSearchPrefillRequest] = useState<{
+    query: string;
+    nonce: number;
+  } | null>(null);
 
   const handleOpenContactInfo = useCallback((publicKey: string, fromChannel?: boolean) => {
     setInfoPaneContactKey(publicKey);
@@ -95,12 +101,30 @@ export function useConversationNavigation({
     [handleSelectConversationWithTargetReset]
   );
 
+  const handleOpenSearchWithQuery = useCallback(
+    (query: string) => {
+      setTargetMessageId(null);
+      setInfoPaneContactKey(null);
+      handleSelectConversationWithTargetReset({
+        type: 'search',
+        id: 'search',
+        name: 'Message Search',
+      });
+      setSearchPrefillRequest((prev) => ({
+        query,
+        nonce: (prev?.nonce ?? 0) + 1,
+      }));
+    },
+    [handleSelectConversationWithTargetReset]
+  );
+
   return {
     targetMessageId,
     setTargetMessageId,
     infoPaneContactKey,
     infoPaneFromChannel,
     infoPaneChannelKey,
+    searchPrefillRequest,
     handleOpenContactInfo,
     handleCloseContactInfo,
     handleOpenChannelInfo,
@@ -108,5 +132,6 @@ export function useConversationNavigation({
     handleSelectConversationWithTargetReset,
     handleNavigateToChannel,
     handleNavigateToMessage,
+    handleOpenSearchWithQuery,
   };
 }

frontend/src/test/appSearchJump.test.tsx

@@ -132,6 +132,7 @@ vi.mock('../components/NewMessageModal', () => ({
 vi.mock('../components/SearchView', () => ({
   SearchView: ({
     onNavigateToMessage,
+    prefillRequest,
   }: {
     onNavigateToMessage: (target: {
       id: number;
@@ -139,20 +140,24 @@ vi.mock('../components/SearchView', () => ({
       conversation_key: string;
       conversation_name: string;
     }) => void;
+    prefillRequest?: { query: string; nonce: number } | null;
   }) => (
-    <button
-      type="button"
-      onClick={() =>
-        onNavigateToMessage({
-          id: 321,
-          type: 'CHAN',
-          conversation_key: PUBLIC_CHANNEL_KEY,
-          conversation_name: 'Public',
-        })
-      }
-    >
-      Jump Result
-    </button>
+    <div>
+      <div data-testid="search-prefill">{prefillRequest?.query ?? ''}</div>
+      <button
+        type="button"
+        onClick={() =>
+          onNavigateToMessage({
+            id: 321,
+            type: 'CHAN',
+            conversation_key: PUBLIC_CHANNEL_KEY,
+            conversation_name: 'Public',
+          })
+        }
+      >
+        Jump Result
+      </button>
+    </div>
   ),
 }));
 
@@ -165,7 +170,15 @@ vi.mock('../components/RawPacketList', () => ({
 }));
 
 vi.mock('../components/ContactInfoPane', () => ({
-  ContactInfoPane: () => null,
+  ContactInfoPane: ({
+    onSearchMessagesByKey,
+  }: {
+    onSearchMessagesByKey?: (publicKey: string) => void;
+  }) => (
+    <button type="button" onClick={() => onSearchMessagesByKey?.('aa'.repeat(32))}>
+      Search Contact By Key
+    </button>
+  ),
 }));
 
 vi.mock('../components/ChannelInfoPane', () => ({
@@ -258,4 +271,23 @@ describe('App search jump target handling', () => {
       expect(lastCall?.[1]).toBeNull();
     });
   });
+
+  it('opens search with a prefilled query from the contact pane', async () => {
+    render(<App />);
+
+    await waitFor(() => {
+      expect(screen.getByText('Search Contact By Key')).toBeInTheDocument();
+    });
+
+    fireEvent.click(screen.getByText('Search Contact By Key'));
+
+    await waitFor(() => {
+      expect(screen.getByTestId('search-prefill')).toHaveTextContent(`user:${'aa'.repeat(32)}`);
+      expect(
+        screen
+          .getAllByTestId('active-conversation')
+          .some((node) => node.textContent === 'search:search')
+      ).toBe(true);
+    });
+  });
 });

frontend/src/test/contactInfoPane.test.tsx

@@ -92,11 +92,15 @@ const baseProps = {
   config: null,
   favorites: [],
   onToggleFavorite: () => {},
+  onSearchMessagesByKey: vi.fn(),
+  onSearchMessagesByName: vi.fn(),
 };
 
 describe('ContactInfoPane', () => {
   beforeEach(() => {
     getContactAnalytics.mockReset();
+    baseProps.onSearchMessagesByKey = vi.fn();
+    baseProps.onSearchMessagesByName = vi.fn();
   });
 
   it('shows hop width when contact has a stored path hash mode', async () => {
@@ -190,9 +194,23 @@ describe('ContactInfoPane', () => {
         screen.getByText(/Name-only analytics include channel messages only/i)
       ).toBeInTheDocument();
       expect(screen.getByText(/same sender name/i)).toBeInTheDocument();
+      expect(screen.getByText("Search user's messages by name")).toBeInTheDocument();
     });
   });
 
+  it('fires the name search callback from the name-only pane', async () => {
+    getContactAnalytics.mockResolvedValue(
+      createAnalytics(null, { lookup_type: 'name', name: 'Mystery' })
+    );
+
+    render(<ContactInfoPane {...baseProps} contactKey="name:Mystery" fromChannel />);
+
+    const button = await screen.findByRole('button', { name: "Search user's messages by name" });
+    button.click();
+
+    expect(baseProps.onSearchMessagesByName).toHaveBeenCalledWith('Mystery');
+  });
+
   it('shows alias note in the channel attribution warning for keyed contacts', async () => {
     const contact = createContact();
     getContactAnalytics.mockResolvedValue(
@@ -214,6 +232,19 @@ describe('ContactInfoPane', () => {
           /may include messages previously attributed under names shown in Also Known As/i
         )
       ).toBeInTheDocument();
+      expect(screen.getByText("Search user's messages by key")).toBeInTheDocument();
     });
   });
+
+  it('fires the key search callback from the keyed pane', async () => {
+    const contact = createContact();
+    getContactAnalytics.mockResolvedValue(createAnalytics(contact));
+
+    render(<ContactInfoPane {...baseProps} contactKey={contact.public_key} />);
+
+    const button = await screen.findByRole('button', { name: "Search user's messages by key" });
+    button.click();
+
+    expect(baseProps.onSearchMessagesByKey).toHaveBeenCalledWith(contact.public_key);
+  });
 });

frontend/src/test/searchView.test.tsx

@@ -70,6 +70,7 @@ describe('SearchView', () => {
     mockGetMessages.mockResolvedValue([]);
     render(<SearchView {...defaultProps} />);
     expect(screen.getByText('Type to search across all messages')).toBeInTheDocument();
+    expect(screen.getByText(/Tip: use/i)).toBeInTheDocument();
   });
 
   it('focuses input on mount', () => {
@@ -246,4 +247,37 @@ describe('SearchView', () => {
 
     expect(screen.getByText('Bob')).toBeInTheDocument();
   });
+
+  it('passes raw operator queries to the API and highlights only free text', async () => {
+    mockGetMessages.mockResolvedValue([createSearchResult({ text: 'hello world' })]);
+
+    render(<SearchView {...defaultProps} />);
+
+    await typeAndWaitForResults('user:Alice hello');
+
+    expect(mockGetMessages).toHaveBeenCalledWith(
+      expect.objectContaining({ q: 'user:Alice hello' }),
+      expect.any(AbortSignal)
+    );
+    expect(screen.getByText('hello', { selector: 'mark' })).toBeInTheDocument();
+    expect(screen.queryByText('user:Alice', { selector: 'mark' })).not.toBeInTheDocument();
+  });
+
+  it('runs a prefilled search immediately', async () => {
+    mockGetMessages.mockResolvedValue([createSearchResult({ text: 'prefilled result' })]);
+
+    render(
+      <SearchView {...defaultProps} prefillRequest={{ query: 'user:"Alice Smith"', nonce: 1 }} />
+    );
+
+    await act(async () => {
+      await new Promise((resolve) => setTimeout(resolve, 0));
+    });
+
+    expect(screen.getByLabelText('Search messages')).toHaveValue('user:"Alice Smith"');
+    expect(mockGetMessages).toHaveBeenCalledWith(
+      expect.objectContaining({ q: 'user:"Alice Smith"' }),
+      expect.any(AbortSignal)
+    );
+  });
 });

tests/e2e/global-setup.ts

@@ -1,6 +1,6 @@
 import type { FullConfig } from '@playwright/test';
 
-const BASE_URL = 'http://localhost:8000';
+const BASE_URL = 'http://localhost:8001';
 const MAX_RETRIES = 10;
 const RETRY_DELAY_MS = 2000;
 

tests/e2e/helpers/api.ts

@@ -3,7 +3,7 @@
  * These bypass the UI to set up preconditions and verify backend state.
  */
 
-const BASE_URL = 'http://localhost:8000/api';
+const BASE_URL = 'http://localhost:8001/api';
 
 async function fetchJson<T>(path: string, init?: RequestInit): Promise<T> {
   const res = await fetch(`${BASE_URL}${path}`, {

tests/e2e/playwright.config.ts

@@ -22,7 +22,7 @@ export default defineConfig({
   reporter: [['list'], ['html', { open: 'never' }]],
 
   use: {
-    baseURL: 'http://localhost:8000',
+    baseURL: 'http://localhost:8001',
     trace: 'on-first-retry',
     screenshot: 'only-on-failure',
   },
@@ -45,10 +45,10 @@ export default defineConfig({
         echo "[e2e] $(date +%T.%3N) frontend/dist exists — skipping build"
       fi
       echo "[e2e] $(date +%T.%3N) Launching uvicorn..."
-      uv run uvicorn app.main:app --host 127.0.0.1 --port 8000
+      uv run uvicorn app.main:app --host 127.0.0.1 --port 8001
     '`,
     cwd: projectRoot,
-    port: 8000,
+    port: 8001,
     reuseExistingServer: false,
     timeout: 180_000,
     env: {

tests/e2e/specs/sidebar-search.spec.ts

@@ -1,21 +1,29 @@
 import { test, expect } from '@playwright/test';
-import { createChannel, deleteChannel, getChannels } from '../helpers/api';
+import { createChannel, createContact, deleteChannel, deleteContact } from '../helpers/api';
 
 test.describe('Sidebar search/filter', () => {
   const suffix = Date.now().toString().slice(-6);
   const nameA = `#alpha${suffix}`;
   const nameB = `#bravo${suffix}`;
+  const contactName = `Search Contact ${suffix}`;
+  const contactKey = `feed${suffix.padStart(8, '0')}${'ab'.repeat(26)}`;
   let keyA = '';
   let keyB = '';
 
   test.beforeAll(async () => {
     const chA = await createChannel(nameA);
     const chB = await createChannel(nameB);
+    await createContact(contactKey, contactName);
     keyA = chA.key;
     keyB = chB.key;
   });
 
   test.afterAll(async () => {
+    try {
+      await deleteContact(contactKey);
+    } catch {
+      // Best-effort cleanup
+    }
     for (const key of [keyA, keyB]) {
       try {
         await deleteChannel(key);
@@ -25,27 +33,40 @@ test.describe('Sidebar search/filter', () => {
     }
   });
 
-  test('search filters conversations by name', async ({ page }) => {
+  test('search filters channel and contact conversations by name and key prefix', async ({
+    page,
+  }) => {
     await page.goto('/');
     await expect(page.getByRole('status', { name: 'Radio OK' })).toBeVisible();
 
-    // Both channels should be visible
+    // Seeded conversations should be visible.
     await expect(page.getByText(nameA, { exact: true })).toBeVisible();
     await expect(page.getByText(nameB, { exact: true })).toBeVisible();
+    await expect(page.getByText(contactName, { exact: true })).toBeVisible();
 
-    // Type partial name to filter
     const searchInput = page.getByLabel('Search conversations');
-    await searchInput.fill(`alpha${suffix}`);
 
-    // Only nameA should be visible
+    // Channel name query should filter to the matching channel only.
+    await searchInput.fill(`alpha${suffix}`);
     await expect(page.getByText(nameA, { exact: true })).toBeVisible();
     await expect(page.getByText(nameB, { exact: true })).not.toBeVisible();
+    await expect(page.getByText(contactName, { exact: true })).not.toBeVisible();
 
-    // Clear search
+    // Contact name query should filter to the matching contact.
+    await searchInput.fill(`contact ${suffix}`);
+    await expect(page.getByText(contactName, { exact: true })).toBeVisible();
+    await expect(page.getByText(nameA, { exact: true })).not.toBeVisible();
+    await expect(page.getByText(nameB, { exact: true })).not.toBeVisible();
+
+    // Contact key prefix query should also match that contact.
+    await searchInput.fill(contactKey.slice(0, 12));
+    await expect(page.getByText(contactName, { exact: true })).toBeVisible();
+    await expect(page.getByText(nameA, { exact: true })).not.toBeVisible();
+
+    // Clear search should restore the full conversation list.
     await page.getByTitle('Clear search').click();
-
-    // Both should return
     await expect(page.getByText(nameA, { exact: true })).toBeVisible();
     await expect(page.getByText(nameB, { exact: true })).toBeVisible();
+    await expect(page.getByText(contactName, { exact: true })).toBeVisible();
   });
 });

tests/test_messages_search.py

@@ -3,7 +3,7 @@
 import pytest
 
 from app.radio import radio_manager
-from app.repository import MessageRepository
+from app.repository import ChannelRepository, ContactRepository, MessageRepository
 
 CHAN_KEY = "ABC123DEF456ABC123DEF456ABC12345"
 DM_KEY = "aa" * 32
@@ -136,6 +136,181 @@ class TestMessageSearch:
         assert len(results) == 1
         assert results[0].sender_name == "Alice"
 
+    @pytest.mark.asyncio
+    async def test_search_user_operator_matches_channel_sender_name(self, test_db):
+        await MessageRepository.create(
+            msg_type="CHAN",
+            text="hello from alice",
+            conversation_key=CHAN_KEY,
+            sender_timestamp=100,
+            received_at=100,
+            sender_name="Alice",
+        )
+        await MessageRepository.create(
+            msg_type="CHAN",
+            text="hello from bob",
+            conversation_key=CHAN_KEY,
+            sender_timestamp=101,
+            received_at=101,
+            sender_name="Bob",
+        )
+
+        results = await MessageRepository.get_all(q='user:"Alice"')
+        assert [message.text for message in results] == ["hello from alice"]
+
+    @pytest.mark.asyncio
+    async def test_search_user_operator_matches_dm_contact_name(self, test_db):
+        await ContactRepository.upsert(
+            {
+                "public_key": DM_KEY,
+                "name": "Alice Smith",
+                "type": 1,
+            }
+        )
+        await MessageRepository.create(
+            msg_type="PRIV",
+            text="hello from dm",
+            conversation_key=DM_KEY,
+            sender_timestamp=100,
+            received_at=100,
+        )
+        await MessageRepository.create(
+            msg_type="PRIV",
+            text="hello from other dm",
+            conversation_key=("bb" * 32),
+            sender_timestamp=101,
+            received_at=101,
+        )
+
+        results = await MessageRepository.get_all(q='user:"Alice Smith"')
+        assert [message.text for message in results] == ["hello from dm"]
+
+    @pytest.mark.asyncio
+    async def test_search_user_operator_matches_key_prefix(self, test_db):
+        await MessageRepository.create(
+            msg_type="PRIV",
+            text="dm by key prefix",
+            conversation_key=DM_KEY,
+            sender_timestamp=100,
+            received_at=100,
+        )
+        await MessageRepository.create(
+            msg_type="CHAN",
+            text="chan by key prefix",
+            conversation_key=CHAN_KEY,
+            sender_timestamp=101,
+            received_at=101,
+            sender_key=DM_KEY,
+            sender_name="Alice",
+        )
+        await MessageRepository.create(
+            msg_type="PRIV",
+            text="other dm",
+            conversation_key=("bb" * 32),
+            sender_timestamp=102,
+            received_at=102,
+        )
+
+        results = await MessageRepository.get_all(q=f"user:{DM_KEY[:12]}")
+        assert [message.text for message in results] == ["chan by key prefix", "dm by key prefix"]
+
+    @pytest.mark.asyncio
+    async def test_search_channel_operator_matches_channel_name(self, test_db):
+        await ChannelRepository.upsert(key=CHAN_KEY, name="#flightless", is_hashtag=True)
+        await ChannelRepository.upsert(key=OTHER_CHAN_KEY, name="#other", is_hashtag=True)
+        await MessageRepository.create(
+            msg_type="CHAN",
+            text="hello flightless",
+            conversation_key=CHAN_KEY,
+            sender_timestamp=100,
+            received_at=100,
+        )
+        await MessageRepository.create(
+            msg_type="CHAN",
+            text="hello elsewhere",
+            conversation_key=OTHER_CHAN_KEY,
+            sender_timestamp=101,
+            received_at=101,
+        )
+
+        results = await MessageRepository.get_all(q='channel:"#flightless"')
+        assert [message.text for message in results] == ["hello flightless"]
+
+    @pytest.mark.asyncio
+    async def test_search_channel_operator_matches_quoted_name_with_spaces(self, test_db):
+        await ChannelRepository.upsert(key=CHAN_KEY, name="#Ops Room", is_hashtag=True)
+        await ChannelRepository.upsert(key=OTHER_CHAN_KEY, name="#Other Room", is_hashtag=True)
+        await MessageRepository.create(
+            msg_type="CHAN",
+            text="hello ops room",
+            conversation_key=CHAN_KEY,
+            sender_timestamp=100,
+            received_at=100,
+        )
+        await MessageRepository.create(
+            msg_type="CHAN",
+            text="hello other room",
+            conversation_key=OTHER_CHAN_KEY,
+            sender_timestamp=101,
+            received_at=101,
+        )
+
+        results = await MessageRepository.get_all(q='channel:"#Ops Room"')
+        assert [message.text for message in results] == ["hello ops room"]
+
+    @pytest.mark.asyncio
+    async def test_search_channel_operator_matches_channel_key_prefix(self, test_db):
+        await MessageRepository.create(
+            msg_type="CHAN",
+            text="chan by key",
+            conversation_key=CHAN_KEY,
+            sender_timestamp=100,
+            received_at=100,
+        )
+        await MessageRepository.create(
+            msg_type="CHAN",
+            text="other channel",
+            conversation_key=OTHER_CHAN_KEY,
+            sender_timestamp=101,
+            received_at=101,
+        )
+
+        results = await MessageRepository.get_all(q=f"channel:{CHAN_KEY[:8]}")
+        assert [message.text for message in results] == ["chan by key"]
+
+    @pytest.mark.asyncio
+    async def test_search_scope_operators_and_free_text_are_combined(self, test_db):
+        await ChannelRepository.upsert(key=CHAN_KEY, name="#flightless", is_hashtag=True)
+        await MessageRepository.create(
+            msg_type="CHAN",
+            text="hello operator",
+            conversation_key=CHAN_KEY,
+            sender_timestamp=100,
+            received_at=100,
+            sender_name="Alice",
+        )
+        await MessageRepository.create(
+            msg_type="CHAN",
+            text="goodbye operator",
+            conversation_key=CHAN_KEY,
+            sender_timestamp=101,
+            received_at=101,
+            sender_name="Alice",
+        )
+        await MessageRepository.create(
+            msg_type="CHAN",
+            text="hello operator",
+            conversation_key=OTHER_CHAN_KEY,
+            sender_timestamp=102,
+            received_at=102,
+            sender_name="Bob",
+        )
+
+        results = await MessageRepository.get_all(
+            q='user:Alice channel:"#flightless" hello operator'
+        )
+        assert [message.text for message in results] == ["hello operator"]
+
 
 class TestMessagesAround:
     """Tests for get_around()."""