diff --git a/packages/coding-agent/CHANGELOG.md b/packages/coding-agent/CHANGELOG.md
index 86a68cd2..92d7c406 100644
--- a/packages/coding-agent/CHANGELOG.md
+++ b/packages/coding-agent/CHANGELOG.md
@@ -12,6 +12,7 @@
 
 - Edit tool now uses fuzzy matching as fallback when exact match fails, tolerating trailing whitespace, smart quotes, Unicode dashes, and special spaces ([#713](https://github.com/badlogic/pi-mono/pull/713) by [@dannote](https://github.com/dannote))
 - Support `APPEND_SYSTEM.md` to append instructions to the system prompt ([#716](https://github.com/badlogic/pi-mono/pull/716) by [@tallshort](https://github.com/tallshort))
+- Session picker search: Ctrl+R toggles sorting between fuzzy match (default) and most recent; supports quoted phrase matching and `re:` regex mode ([#731](https://github.com/badlogic/pi-mono/pull/731) by [@ogulcancelik](https://github.com/ogulcancelik))
 
 ### Changed
 
diff --git a/packages/coding-agent/src/modes/interactive/components/session-selector-search.ts b/packages/coding-agent/src/modes/interactive/components/session-selector-search.ts
new file mode 100644
index 00000000..b77d2f88
--- /dev/null
+++ b/packages/coding-agent/src/modes/interactive/components/session-selector-search.ts
@@ -0,0 +1,176 @@
+import { fuzzyMatch } from "@mariozechner/pi-tui";
+import type { SessionInfo } from "../../../core/session-manager.js";
+
+export type SortMode = "recent" | "relevance";
+
+export interface ParsedSearchQuery {
+	mode: "tokens" | "regex";
+	tokens: { kind: "fuzzy" | "phrase"; value: string }[];
+	regex: RegExp | null;
+	/** If set, parsing failed and we should treat query as non-matching. */
+	error?: string;
+}
+
+export interface MatchResult {
+	matches: boolean;
+	/** Lower is better; only meaningful when matches === true */
+	score: number;
+}
+
+function normalizeWhitespaceLower(text: string): string {
+	return text.toLowerCase().replace(/\s+/g, " ").trim();
+}
+
+function getSessionSearchText(session: SessionInfo): string {
+	return `${session.id} ${session.name ?? ""} ${session.allMessagesText} ${session.cwd}`;
+}
+
+export function parseSearchQuery(query: string): ParsedSearchQuery {
+	const trimmed = query.trim();
+	if (!trimmed) {
+		return { mode: "tokens", tokens: [], regex: null };
+	}
+
+	// Regex mode: re:<pattern>
+	if (trimmed.startsWith("re:")) {
+		const pattern = trimmed.slice(3).trim();
+		if (!pattern) {
+			return { mode: "regex", tokens: [], regex: null, error: "Empty regex" };
+		}
+		try {
+			return { mode: "regex", tokens: [], regex: new RegExp(pattern, "i") };
+		} catch (err) {
+			const msg = err instanceof Error ? err.message : String(err);
+			return { mode: "regex", tokens: [], regex: null, error: msg };
+		}
+	}
+
+	// Token mode with quote support.
+	// Example: foo "node cve" bar
+	const tokens: { kind: "fuzzy" | "phrase"; value: string }[] = [];
+	let buf = "";
+	let inQuote = false;
+	let hadUnclosedQuote = false;
+
+	const flush = (kind: "fuzzy" | "phrase"): void => {
+		const v = buf.trim();
+		buf = "";
+		if (!v) return;
+		tokens.push({ kind, value: v });
+	};
+
+	for (let i = 0; i < trimmed.length; i++) {
+		const ch = trimmed[i]!;
+		if (ch === '"') {
+			if (inQuote) {
+				flush("phrase");
+				inQuote = false;
+			} else {
+				flush("fuzzy");
+				inQuote = true;
+			}
+			continue;
+		}
+
+		if (!inQuote && /\s/.test(ch)) {
+			flush("fuzzy");
+			continue;
+		}
+
+		buf += ch;
+	}
+
+	if (inQuote) {
+		hadUnclosedQuote = true;
+	}
+
+	// If quotes were unbalanced, fall back to plain whitespace tokenization.
+	if (hadUnclosedQuote) {
+		return {
+			mode: "tokens",
+			tokens: trimmed
+				.split(/\s+/)
+				.map((t) => t.trim())
+				.filter((t) => t.length > 0)
+				.map((t) => ({ kind: "fuzzy" as const, value: t })),
+			regex: null,
+		};
+	}
+
+	flush(inQuote ? "phrase" : "fuzzy");
+
+	return { mode: "tokens", tokens, regex: null };
+}
+
+export function matchSession(session: SessionInfo, parsed: ParsedSearchQuery): MatchResult {
+	const text = getSessionSearchText(session);
+
+	if (parsed.mode === "regex") {
+		if (!parsed.regex) {
+			return { matches: false, score: 0 };
+		}
+		const idx = text.search(parsed.regex);
+		if (idx < 0) return { matches: false, score: 0 };
+		return { matches: true, score: idx * 0.1 };
+	}
+
+	if (parsed.tokens.length === 0) {
+		return { matches: true, score: 0 };
+	}
+
+	let totalScore = 0;
+	let normalizedText: string | null = null;
+
+	for (const token of parsed.tokens) {
+		if (token.kind === "phrase") {
+			if (normalizedText === null) {
+				normalizedText = normalizeWhitespaceLower(text);
+			}
+			const phrase = normalizeWhitespaceLower(token.value);
+			if (!phrase) continue;
+			const idx = normalizedText.indexOf(phrase);
+			if (idx < 0) return { matches: false, score: 0 };
+			totalScore += idx * 0.1;
+			continue;
+		}
+
+		const m = fuzzyMatch(token.value, text);
+		if (!m.matches) return { matches: false, score: 0 };
+		totalScore += m.score;
+	}
+
+	return { matches: true, score: totalScore };
+}
+
+export function filterAndSortSessions(sessions: SessionInfo[], query: string, sortMode: SortMode): SessionInfo[] {
+	const trimmed = query.trim();
+	if (!trimmed) return sessions;
+
+	const parsed = parseSearchQuery(query);
+	if (parsed.error) return [];
+
+	// Recent mode: filter only, keep incoming order.
+	if (sortMode === "recent") {
+		const filtered: SessionInfo[] = [];
+		for (const s of sessions) {
+			const res = matchSession(s, parsed);
+			if (res.matches) filtered.push(s);
+		}
+		return filtered;
+	}
+
+	// Relevance mode: sort by score, tie-break by modified desc.
+	const scored: { session: SessionInfo; score: number }[] = [];
+	for (const s of sessions) {
+		const res = matchSession(s, parsed);
+		if (!res.matches) continue;
+		scored.push({ session: s, score: res.score });
+	}
+
+	scored.sort((a, b) => {
+		if (a.score !== b.score) return a.score - b.score;
+		return b.session.modified.getTime() - a.session.modified.getTime();
+	});
+
+	return scored.map((r) => r.session);
+}
diff --git a/packages/coding-agent/src/modes/interactive/components/session-selector.ts b/packages/coding-agent/src/modes/interactive/components/session-selector.ts
index 911291da..191066d8 100644
--- a/packages/coding-agent/src/modes/interactive/components/session-selector.ts
+++ b/packages/coding-agent/src/modes/interactive/components/session-selector.ts
@@ -2,9 +2,9 @@ import * as os from "node:os";
 import {
 	type Component,
 	Container,
-	fuzzyFilter,
 	getEditorKeybindings,
 	Input,
+	matchesKey,
 	Spacer,
 	truncateToWidth,
 	visibleWidth,
@@ -12,6 +12,7 @@ import {
 import type { SessionInfo, SessionListProgress } from "../../../core/session-manager.js";
 import { theme } from "../theme/theme.js";
 import { DynamicBorder } from "./dynamic-border.js";
+import { filterAndSortSessions, type SortMode } from "./session-selector-search.js";
 
 type SessionScope = "current" | "all";
 
@@ -42,17 +43,23 @@ function formatSessionDate(date: Date): string {
 
 class SessionSelectorHeader implements Component {
 	private scope: SessionScope;
+	private sortMode: SortMode;
 	private loading = false;
 	private loadProgress: { loaded: number; total: number } | null = null;
 
-	constructor(scope: SessionScope) {
+	constructor(scope: SessionScope, sortMode: SortMode) {
 		this.scope = scope;
+		this.sortMode = sortMode;
 	}
 
 	setScope(scope: SessionScope): void {
 		this.scope = scope;
 	}
 
+	setSortMode(sortMode: SortMode): void {
+		this.sortMode = sortMode;
+	}
+
 	setLoading(loading: boolean): void {
 		this.loading = loading;
 		if (!loading) {
@@ -69,6 +76,10 @@ class SessionSelectorHeader implements Component {
 	render(width: number): string[] {
 		const title = this.scope === "current" ? "Resume Session (Current Folder)" : "Resume Session (All)";
 		const leftText = theme.bold(title);
+
+		const sortLabel = this.sortMode === "recent" ? "Recent" : "Fuzzy";
+		const sortText = theme.fg("muted", "Sort: ") + theme.fg("accent", sortLabel);
+
 		let scopeText: string;
 		if (this.loading) {
 			const progressText = this.loadProgress ? `${this.loadProgress.loaded}/${this.loadProgress.total}` : "...";
@@ -79,11 +90,12 @@ class SessionSelectorHeader implements Component {
 					? `${theme.fg("accent", "◉ Current Folder")}${theme.fg("muted", " | ○ All")}`
 					: `${theme.fg("muted", "○ Current Folder | ")}${theme.fg("accent", "◉ All")}`;
 		}
-		const rightText = truncateToWidth(scopeText, width, "");
+
+		const rightText = truncateToWidth(`${scopeText}  ${sortText}`, width, "");
 		const availableLeft = Math.max(0, width - visibleWidth(rightText) - 1);
 		const left = truncateToWidth(leftText, availableLeft, "");
 		const spacing = Math.max(0, width - visibleWidth(left) - visibleWidth(rightText));
-		const hint = theme.fg("muted", "Tab to toggle scope");
+		const hint = theme.fg("muted", 'Tab: scope · Ctrl+R: sort · re:<pattern> for regex · "phrase" for exact phrase');
 		return [`${left}${" ".repeat(spacing)}${rightText}`, hint];
 	}
 }
@@ -97,17 +109,20 @@ class SessionList implements Component {
 	private selectedIndex: number = 0;
 	private searchInput: Input;
 	private showCwd = false;
+	private sortMode: SortMode = "relevance";
 	public onSelect?: (sessionPath: string) => void;
 	public onCancel?: () => void;
 	public onExit: () => void = () => {};
 	public onToggleScope?: () => void;
+	public onToggleSort?: () => void;
 	private maxVisible: number = 5; // Max sessions visible (each session is 3 lines: msg + metadata + blank)
 
-	constructor(sessions: SessionInfo[], showCwd: boolean) {
+	constructor(sessions: SessionInfo[], showCwd: boolean, sortMode: SortMode) {
 		this.allSessions = sessions;
 		this.filteredSessions = sessions;
 		this.searchInput = new Input();
 		this.showCwd = showCwd;
+		this.sortMode = sortMode;
 
 		// Handle Enter in search input - select current item
 		this.searchInput.onSubmit = () => {
@@ -120,6 +135,11 @@ class SessionList implements Component {
 		};
 	}
 
+	setSortMode(sortMode: SortMode): void {
+		this.sortMode = sortMode;
+		this.filterSessions(this.searchInput.getValue());
+	}
+
 	setSessions(sessions: SessionInfo[], showCwd: boolean): void {
 		this.allSessions = sessions;
 		this.showCwd = showCwd;
@@ -127,11 +147,7 @@ class SessionList implements Component {
 	}
 
 	private filterSessions(query: string): void {
-		this.filteredSessions = fuzzyFilter(
-			this.allSessions,
-			query,
-			(session) => `${session.id} ${session.name ?? ""} ${session.allMessagesText} ${session.cwd}`,
-		);
+		this.filteredSessions = filterAndSortSessions(this.allSessions, query, this.sortMode);
 		this.selectedIndex = Math.min(this.selectedIndex, Math.max(0, this.filteredSessions.length - 1));
 	}
 
@@ -219,6 +235,12 @@ class SessionList implements Component {
 			}
 			return;
 		}
+
+		if (matchesKey(keyData, "ctrl+r")) {
+			this.onToggleSort?.();
+			return;
+		}
+
 		// Up arrow
 		if (kb.matches(keyData, "selectUp")) {
 			this.selectedIndex = Math.max(0, this.selectedIndex - 1);
@@ -265,6 +287,7 @@ export class SessionSelectorComponent extends Container {
 	private sessionList: SessionList;
 	private header: SessionSelectorHeader;
 	private scope: SessionScope = "current";
+	private sortMode: SortMode = "relevance";
 	private currentSessions: SessionInfo[] | null = null;
 	private allSessions: SessionInfo[] | null = null;
 	private currentSessionsLoader: SessionsLoader;
@@ -285,7 +308,7 @@ export class SessionSelectorComponent extends Container {
 		this.allSessionsLoader = allSessionsLoader;
 		this.onCancel = onCancel;
 		this.requestRender = requestRender;
-		this.header = new SessionSelectorHeader(this.scope);
+		this.header = new SessionSelectorHeader(this.scope, this.sortMode);
 
 		// Add header
 		this.addChild(new Spacer(1));
@@ -295,11 +318,12 @@ export class SessionSelectorComponent extends Container {
 		this.addChild(new Spacer(1));
 
 		// Create session list (starts empty, will be populated after load)
-		this.sessionList = new SessionList([], false);
+		this.sessionList = new SessionList([], false, this.sortMode);
 		this.sessionList.onSelect = onSelect;
 		this.sessionList.onCancel = onCancel;
 		this.sessionList.onExit = onExit;
 		this.sessionList.onToggleScope = () => this.toggleScope();
+		this.sessionList.onToggleSort = () => this.toggleSortMode();
 
 		this.addChild(this.sessionList);
 
@@ -325,6 +349,13 @@ export class SessionSelectorComponent extends Container {
 		});
 	}
 
+	private toggleSortMode(): void {
+		this.sortMode = this.sortMode === "recent" ? "relevance" : "recent";
+		this.header.setSortMode(this.sortMode);
+		this.sessionList.setSortMode(this.sortMode);
+		this.requestRender();
+	}
+
 	private toggleScope(): void {
 		if (this.scope === "current") {
 			// Switching to "all" - load if not already loaded
diff --git a/packages/coding-agent/test/session-selector-search.test.ts b/packages/coding-agent/test/session-selector-search.test.ts
new file mode 100644
index 00000000..00d66606
--- /dev/null
+++ b/packages/coding-agent/test/session-selector-search.test.ts
@@ -0,0 +1,127 @@
+import { describe, expect, it } from "vitest";
+import type { SessionInfo } from "../src/core/session-manager.js";
+import { filterAndSortSessions } from "../src/modes/interactive/components/session-selector-search.js";
+
+function makeSession(
+	overrides: Partial<SessionInfo> & { id: string; modified: Date; allMessagesText: string },
+): SessionInfo {
+	return {
+		path: `/tmp/${overrides.id}.jsonl`,
+		id: overrides.id,
+		cwd: overrides.cwd ?? "",
+		name: overrides.name,
+		created: overrides.created ?? new Date(0),
+		modified: overrides.modified,
+		messageCount: overrides.messageCount ?? 1,
+		firstMessage: overrides.firstMessage ?? "(no messages)",
+		allMessagesText: overrides.allMessagesText,
+	};
+}
+
+describe("session selector search", () => {
+	it("filters by quoted phrase with whitespace normalization", () => {
+		const sessions: SessionInfo[] = [
+			makeSession({
+				id: "a",
+				modified: new Date("2026-01-01T00:00:00.000Z"),
+				allMessagesText: "node\n\n   cve was discussed",
+			}),
+			makeSession({
+				id: "b",
+				modified: new Date("2026-01-02T00:00:00.000Z"),
+				allMessagesText: "node something else",
+			}),
+		];
+
+		const result = filterAndSortSessions(sessions, '"node cve"', "recent");
+		expect(result.map((s) => s.id)).toEqual(["a"]);
+	});
+
+	it("filters by regex (re:) and is case-insensitive", () => {
+		const sessions: SessionInfo[] = [
+			makeSession({
+				id: "a",
+				modified: new Date("2026-01-02T00:00:00.000Z"),
+				allMessagesText: "Brave is great",
+			}),
+			makeSession({
+				id: "b",
+				modified: new Date("2026-01-03T00:00:00.000Z"),
+				allMessagesText: "bravery is not the same",
+			}),
+		];
+
+		const result = filterAndSortSessions(sessions, "re:\\bbrave\\b", "recent");
+		expect(result.map((s) => s.id)).toEqual(["a"]);
+	});
+
+	it("recent sort preserves input order", () => {
+		const sessions: SessionInfo[] = [
+			makeSession({
+				id: "newer",
+				modified: new Date("2026-01-03T00:00:00.000Z"),
+				allMessagesText: "brave",
+			}),
+			makeSession({
+				id: "older",
+				modified: new Date("2026-01-01T00:00:00.000Z"),
+				allMessagesText: "brave",
+			}),
+			makeSession({
+				id: "nomatch",
+				modified: new Date("2026-01-04T00:00:00.000Z"),
+				allMessagesText: "something else",
+			}),
+		];
+
+		const result = filterAndSortSessions(sessions, '"brave"', "recent");
+		expect(result.map((s) => s.id)).toEqual(["newer", "older"]);
+	});
+
+	it("relevance sort orders by score and tie-breaks by modified desc", () => {
+		const sessions: SessionInfo[] = [
+			makeSession({
+				id: "late",
+				modified: new Date("2026-01-03T00:00:00.000Z"),
+				allMessagesText: "xxxx brave",
+			}),
+			makeSession({
+				id: "early",
+				modified: new Date("2026-01-01T00:00:00.000Z"),
+				allMessagesText: "brave xxxx",
+			}),
+		];
+
+		const result1 = filterAndSortSessions(sessions, '"brave"', "relevance");
+		expect(result1.map((s) => s.id)).toEqual(["early", "late"]);
+
+		const tieSessions: SessionInfo[] = [
+			makeSession({
+				id: "newer",
+				modified: new Date("2026-01-03T00:00:00.000Z"),
+				allMessagesText: "brave",
+			}),
+			makeSession({
+				id: "older",
+				modified: new Date("2026-01-01T00:00:00.000Z"),
+				allMessagesText: "brave",
+			}),
+		];
+
+		const result2 = filterAndSortSessions(tieSessions, '"brave"', "relevance");
+		expect(result2.map((s) => s.id)).toEqual(["newer", "older"]);
+	});
+
+	it("returns empty list for invalid regex", () => {
+		const sessions: SessionInfo[] = [
+			makeSession({
+				id: "a",
+				modified: new Date("2026-01-01T00:00:00.000Z"),
+				allMessagesText: "brave",
+			}),
+		];
+
+		const result = filterAndSortSessions(sessions, "re:(", "recent");
+		expect(result).toEqual([]);
+	});
+});