diff --git a/workers/durableObject/index.ts b/workers/durableObject/index.ts
index e2cbbfa3..e584d32c 100644
--- a/workers/durableObject/index.ts
+++ b/workers/durableObject/index.ts
@@ -35,6 +35,21 @@ const ALLOWED_SORT_COLUMNS = [
 
 type SortColumn = (typeof ALLOWED_SORT_COLUMNS)[number];
 
+const SQLITE_LIKE_PATTERN_LIMIT = 50;
+const LIKE_WILDCARD_PADDING = 2;
+const MAX_LIKE_TERM_LENGTH = SQLITE_LIKE_PATTERN_LIMIT - LIKE_WILDCARD_PADDING;
+
+function splitLikeTerm(value: string): string[] {
+	const trimmed = value.trim();
+	if (!trimmed) return [];
+
+	const chunks: string[] = [];
+	for (let i = 0; i < trimmed.length; i += MAX_LIKE_TERM_LENGTH) {
+		chunks.push(trimmed.slice(i, i + MAX_LIKE_TERM_LENGTH));
+	}
+	return chunks;
+}
+
 /**
  * Map SortColumn string names to Drizzle column references for safe
  * ORDER BY construction (no string interpolation into SQL).
@@ -671,20 +686,35 @@ export class MailboxDO extends DurableObject<Env> {
 			return `?${paramIdx}`;
 		};
 
+		const addLikeConditions = (columns: string[], value: string) => {
+			for (const term of splitLikeTerm(value)) {
+				const columnConditions = columns.map(
+					(column) => `${column} LIKE ${addParam(`%${term}%`)}`,
+				);
+				conditions.push(`(${columnConditions.join(" OR ")})`);
+			}
+		};
+
 		if (query) {
-			const p1 = addParam(`%${query}%`);
-			const p2 = addParam(`%${query}%`);
-			const p3 = addParam(`%${query}%`);
-			const p4 = addParam(`%${query}%`);
-			conditions.push(`(${prefix}subject LIKE ${p1} OR ${prefix}body LIKE ${p2} OR ${prefix}sender LIKE ${p3} OR ${prefix}recipient LIKE ${p4} OR ${prefix}cc LIKE ${p4} OR ${prefix}bcc LIKE ${p4})`);
+			addLikeConditions(
+				[
+					`${prefix}subject`,
+					`${prefix}body`,
+					`${prefix}sender`,
+					`${prefix}recipient`,
+					`${prefix}cc`,
+					`${prefix}bcc`,
+				],
+				query,
+			);
 		}
 		if (folder) {
 			const p = addParam(folder);
 			conditions.push(`${prefix}folder_id = (SELECT id FROM folders WHERE name = ${p} OR id = ${p} LIMIT 1)`);
 		}
-		if (from) { const p = addParam(`%${from}%`); conditions.push(`${prefix}sender LIKE ${p}`); }
-		if (to) { const p = addParam(`%${to}%`); conditions.push(`(${prefix}recipient LIKE ${p} OR ${prefix}cc LIKE ${p} OR ${prefix}bcc LIKE ${p})`); }
-		if (subject) { const p = addParam(`%${subject}%`); conditions.push(`${prefix}subject LIKE ${p}`); }
+		if (from) addLikeConditions([`${prefix}sender`], from);
+		if (to) addLikeConditions([`${prefix}recipient`, `${prefix}cc`, `${prefix}bcc`], to);
+		if (subject) addLikeConditions([`${prefix}subject`], subject);
 		if (date_start) { const p = addParam(date_start); conditions.push(`${prefix}date >= ${p}`); }
 		if (date_end) { const p = addParam(date_end); conditions.push(`${prefix}date <= ${p}`); }
 		if (is_read !== undefined) { const p = addParam(is_read ? 1 : 0); conditions.push(`${prefix}read = ${p}`); }