diff --git a/internal/repository/pg_unibox.go b/internal/repository/pg_unibox.go
index 3e512d912..e8a1e9446 100644
--- a/internal/repository/pg_unibox.go
+++ b/internal/repository/pg_unibox.go
@@ -519,7 +519,7 @@ func (r *uniboxRepository) Search(ctx context.Context, orgID uuid.UUID, params *
 		// declares it, or the index is not used.
 		q := *params.Subject
 		webPos, addrPos := argPos, argPos+1
-		args = append(args, q, q)
+		args = append(args, q, escapeLikePattern(q))
 		argPos += 2
 
 		match := fmt.Sprintf(`ue.search_tsv @@ websearch_to_tsquery('english', $%d)
@@ -536,9 +536,9 @@ func (r *uniboxRepository) Search(ctx context.Context, orgID uuid.UUID, params *
 		// Participants. The stored header is "Display Name (addr)", so one
 		// substring match covers searching by either.
 		match += fmt.Sprintf(`
-				OR EXISTS (SELECT 1 FROM unnest(ue.from_addr) AS s(addr) WHERE s.addr ILIKE '%%' || $%d || '%%')
-				OR EXISTS (SELECT 1 FROM unnest(ue.to_addr)   AS s(addr) WHERE s.addr ILIKE '%%' || $%d || '%%')
-				OR EXISTS (SELECT 1 FROM unnest(ue.cc)        AS s(addr) WHERE s.addr ILIKE '%%' || $%d || '%%')`,
+				OR EXISTS (SELECT 1 FROM unnest(ue.from_addr) AS s(addr) WHERE s.addr ILIKE '%%' || $%d || '%%' ESCAPE '\')
+				OR EXISTS (SELECT 1 FROM unnest(ue.to_addr)   AS s(addr) WHERE s.addr ILIKE '%%' || $%d || '%%' ESCAPE '\')
+				OR EXISTS (SELECT 1 FROM unnest(ue.cc)        AS s(addr) WHERE s.addr ILIKE '%%' || $%d || '%%' ESCAPE '\')`,
 			addrPos, addrPos, addrPos)
 
 		inner += ` AND (` + match + `)`
@@ -1494,6 +1494,9 @@ func (r *uniboxRepository) scanGrounding(ctx context.Context, query string, orgI
 // so adding a word narrows rather than widens.
 func prefixTSQuery(input string) string {
 	const maxTerms = 8
+	if hasWebSearchSyntax(input) {
+		return ""
+	}
 
 	cleaned := strings.Map(func(r rune) rune {
 		switch {
@@ -1509,10 +1512,26 @@ func prefixTSQuery(input string) string {
 		return ""
 	}
 	if len(terms) > maxTerms {
-		terms = terms[:maxTerms]
+		return ""
 	}
 	for i, t := range terms {
 		terms[i] = t + ":*"
 	}
 	return strings.Join(terms, " & ")
 }
+
+func hasWebSearchSyntax(input string) bool {
+	if strings.Contains(input, `"`) {
+		return true
+	}
+	for _, term := range strings.Fields(input) {
+		if strings.HasPrefix(term, "-") || strings.EqualFold(term, "OR") {
+			return true
+		}
+	}
+	return false
+}
+
+func escapeLikePattern(input string) string {
+	return strings.NewReplacer(`\`, `\\`, `%`, `\%`, `_`, `\_`).Replace(input)
+}
diff --git a/internal/repository/unibox_search_test.go b/internal/repository/unibox_search_test.go
index 76453a9bd..89ffa4308 100644
--- a/internal/repository/unibox_search_test.go
+++ b/internal/repository/unibox_search_test.go
@@ -19,8 +19,10 @@ func TestPrefixTSQuery(t *testing.T) {
 		// Every one of these makes to_tsquery raise when passed through raw.
 		{"operators are stripped", "a & b | c", "a:* & b:* & c:*"},
 		{"unbalanced bracket", "re: (urgent", "re:* & urgent:*"},
-		{"negation and colons", "!foo:bar", "foo:* & bar:*"},
-		{"quotes", `"exact phrase"`, "exact:* & phrase:*"},
+		{"punctuation and colons", "!foo:bar", "foo:* & bar:*"},
+		{"negation keeps web-search semantics", "foo -bar", ""},
+		{"quotes keep web-search semantics", `"exact phrase"`, ""},
+		{"OR keeps web-search semantics", "foo OR bar", ""},
 		{"a lone operator has nothing to search", "&&&", ""},
 
 		{"empty", "", ""},
@@ -37,11 +39,17 @@ func TestPrefixTSQuery(t *testing.T) {
 	}
 }
 
-// A pasted paragraph must not become a 200-term query the planner has to walk.
+// Long input stays on websearch_to_tsquery instead of being broadened by a truncated prefix query.
 func TestPrefixTSQueryCapsTerms(t *testing.T) {
 	got := prefixTSQuery("one two three four five six seven eight nine ten eleven")
-	want := "one:* & two:* & three:* & four:* & five:* & six:* & seven:* & eight:*"
+	want := ""
 	if got != want {
-		t.Fatalf("prefixTSQuery capped = %q, want %q", got, want)
+		t.Fatalf("prefixTSQuery long input = %q, want %q", got, want)
+	}
+}
+
+func TestEscapeLikePattern(t *testing.T) {
+	if got, want := escapeLikePattern(`100%_done\later`), `100\%\_done\\later`; got != want {
+		t.Fatalf("escapeLikePattern = %q, want %q", got, want)
 	}
 }
diff --git a/web/src/components/app/unibox/ConversationList.tsx b/web/src/components/app/unibox/ConversationList.tsx
index b3087532c..88ae320cf 100644
--- a/web/src/components/app/unibox/ConversationList.tsx
+++ b/web/src/components/app/unibox/ConversationList.tsx
@@ -304,7 +304,7 @@ export function ConversationList({
             // The box searches people, subject and message body, and naming
             // that is the difference between it looking broken and looking
             // useful: nobody tries an address in a box labelled "Search inbox".
-            placeholder={`Search ${scopeLabel.toLowerCase()} — name, address, or any word`}
+            placeholder={`Search ${scopeLabel.toLowerCase()}: name, address, or any word`}
             title={'Searches the sender, recipients, subject and message body. "quoted phrases", OR and -exclude work.'}
             className="flex-1 min-w-0 h-full bg-transparent text-[12.5px] text-slate-900 placeholder:text-slate-400 outline-none"
           />