diff --git a/cli/src/api/apiMachine.ts b/cli/src/api/apiMachine.ts
index fad02bfd..0415c617 100644
--- a/cli/src/api/apiMachine.ts
+++ b/cli/src/api/apiMachine.ts
@@ -3,6 +3,7 @@
  */
 
 import { io, type Socket } from 'socket.io-client'
+import { stat } from 'node:fs/promises'
 import { logger } from '@/ui/logger'
 import { configuration } from '@/configuration'
 import type { DaemonState, Machine, MachineMetadata, Update, UpdateMachineBody } from './types'
@@ -51,6 +52,14 @@ type MachineRpcHandlers = {
     requestShutdown: () => void
 }
 
+interface PathExistsRequest {
+    paths: string[]
+}
+
+interface PathExistsResponse {
+    exists: Record<string, boolean>
+}
+
 export class ApiMachineClient {
     private socket!: Socket<ServerToDaemonEvents, DaemonToServerEvents>
     private keepAliveInterval: NodeJS.Timeout | null = null
@@ -66,6 +75,25 @@ export class ApiMachineClient {
         })
 
         registerCommonHandlers(this.rpcHandlerManager, process.cwd())
+
+        this.rpcHandlerManager.registerHandler<PathExistsRequest, PathExistsResponse>('path-exists', async (params) => {
+            const rawPaths = Array.isArray(params?.paths) ? params.paths : []
+            const uniquePaths = Array.from(new Set(rawPaths.filter((path): path is string => typeof path === 'string')))
+            const exists: Record<string, boolean> = {}
+
+            await Promise.all(uniquePaths.map(async (path) => {
+                const trimmed = path.trim()
+                if (!trimmed) return
+                try {
+                    const stats = await stat(trimmed)
+                    exists[trimmed] = stats.isDirectory()
+                } catch {
+                    exists[trimmed] = false
+                }
+            }))
+
+            return { exists }
+        })
     }
 
     setRPCHandlers({ spawnSession, stopSession, requestShutdown }: MachineRpcHandlers): void {
diff --git a/server/src/sync/syncEngine.ts b/server/src/sync/syncEngine.ts
index 6e4ec49d..aa4c7c9f 100644
--- a/server/src/sync/syncEngine.ts
+++ b/server/src/sync/syncEngine.ts
@@ -133,16 +133,8 @@ export type RpcReadFileResponse = {
     error?: string
 }
 
-export type SlashCommand = {
-    name: string
-    description?: string
-    source: 'builtin' | 'user'
-}
-
-export type RpcSlashCommandsResponse = {
-    success: boolean
-    commands?: SlashCommand[]
-    error?: string
+export type RpcPathExistsResponse = {
+    exists: Record<string, boolean>
 }
 
 export type SyncEventType =
@@ -697,6 +689,24 @@ export class SyncEngine {
         }
     }
 
+    async checkPathsExist(machineId: string, paths: string[]): Promise<Record<string, boolean>> {
+        const result = await this.machineRpc(machineId, 'path-exists', { paths }) as RpcPathExistsResponse | unknown
+        if (!result || typeof result !== 'object') {
+            throw new Error('Unexpected path-exists result')
+        }
+
+        const existsValue = (result as RpcPathExistsResponse).exists
+        if (!existsValue || typeof existsValue !== 'object') {
+            throw new Error('Unexpected path-exists result')
+        }
+
+        const exists: Record<string, boolean> = {}
+        for (const [key, value] of Object.entries(existsValue)) {
+            exists[key] = value === true
+        }
+        return exists
+    }
+
     async getGitStatus(sessionId: string, cwd?: string): Promise<RpcCommandResponse> {
         return await this.sessionRpc(sessionId, 'git-status', { cwd }) as RpcCommandResponse
     }
@@ -717,10 +727,6 @@ export class SyncEngine {
         return await this.sessionRpc(sessionId, 'ripgrep', { args, cwd }) as RpcCommandResponse
     }
 
-    async listSlashCommands(sessionId: string, agent: string): Promise<RpcSlashCommandsResponse> {
-        return await this.sessionRpc(sessionId, 'listSlashCommands', { agent }) as RpcSlashCommandsResponse
-    }
-
     private async sessionRpc(sessionId: string, method: string, params: unknown): Promise<unknown> {
         return await this.rpcCall(`${sessionId}:${method}`, params)
     }
diff --git a/server/src/web/routes/machines.ts b/server/src/web/routes/machines.ts
index bed2ba62..9043d2de 100644
--- a/server/src/web/routes/machines.ts
+++ b/server/src/web/routes/machines.ts
@@ -11,6 +11,10 @@ const spawnBodySchema = z.object({
     worktreeName: z.string().optional()
 })
 
+const pathsExistsSchema = z.object({
+    paths: z.array(z.string().min(1)).max(1000)
+})
+
 export function createMachinesRoutes(getSyncEngine: () => SyncEngine | null): Hono<WebAppEnv> {
     const app = new Hono<WebAppEnv>()
 
@@ -53,5 +57,36 @@ export function createMachinesRoutes(getSyncEngine: () => SyncEngine | null): Ho
         return c.json(result)
     })
 
+    app.post('/machines/:id/paths/exists', async (c) => {
+        const engine = getSyncEngine()
+        if (!engine) {
+            return c.json({ error: 'Not connected' }, 503)
+        }
+
+        const machineId = c.req.param('id')
+        const machine = engine.getMachine(machineId)
+        if (!machine) {
+            return c.json({ error: 'Machine not found' }, 404)
+        }
+
+        const body = await c.req.json().catch(() => null)
+        const parsed = pathsExistsSchema.safeParse(body)
+        if (!parsed.success) {
+            return c.json({ error: 'Invalid body' }, 400)
+        }
+
+        const uniquePaths = Array.from(new Set(parsed.data.paths.map((path) => path.trim()).filter(Boolean)))
+        if (uniquePaths.length === 0) {
+            return c.json({ exists: {} })
+        }
+
+        try {
+            const exists = await engine.checkPathsExist(machineId, uniquePaths)
+            return c.json({ exists })
+        } catch (error) {
+            return c.json({ error: error instanceof Error ? error.message : 'Failed to check paths' }, 500)
+        }
+    })
+
     return app
 }
diff --git a/server/src/web/routes/sessions.ts b/server/src/web/routes/sessions.ts
index 025ab66e..f6c96337 100644
--- a/server/src/web/routes/sessions.ts
+++ b/server/src/web/routes/sessions.ts
@@ -7,6 +7,7 @@ import { requireSessionFromParam, requireSyncEngine } from './guards'
 type SessionSummaryMetadata = {
     name?: string
     path: string
+    machineId?: string
     summary?: { text: string }
     flavor?: string | null
     worktree?: {
@@ -35,6 +36,7 @@ function toSessionSummary(session: Session): SessionSummary {
     const metadata: SessionSummaryMetadata | null = session.metadata ? {
         name: session.metadata.name,
         path: session.metadata.path,
+        machineId: session.metadata.machineId ?? undefined,
         summary: session.metadata.summary ? { text: session.metadata.summary.text } : undefined,
         flavor: session.metadata.flavor ?? null,
         worktree: session.metadata.worktree
diff --git a/web/src/api/client.ts b/web/src/api/client.ts
index 595f5d24..c9b88da6 100644
--- a/web/src/api/client.ts
+++ b/web/src/api/client.ts
@@ -3,6 +3,7 @@ import type {
     FileReadResponse,
     FileSearchResponse,
     GitCommandResponse,
+    MachinePathsExistsResponse,
     MachinesResponse,
     MessagesResponse,
     SlashCommandsResponse,
@@ -228,6 +229,19 @@ export class ApiClient {
         return await this.request<MachinesResponse>('/api/machines')
     }
 
+    async checkMachinePathsExists(
+        machineId: string,
+        paths: string[]
+    ): Promise<MachinePathsExistsResponse> {
+        return await this.request<MachinePathsExistsResponse>(
+            `/api/machines/${encodeURIComponent(machineId)}/paths/exists`,
+            {
+                method: 'POST',
+                body: JSON.stringify({ paths })
+            }
+        )
+    }
+
     async spawnSession(
         machineId: string,
         directory: string,
diff --git a/web/src/components/NewSession.tsx b/web/src/components/NewSession.tsx
index 2ec16595..d294f4d0 100644
--- a/web/src/components/NewSession.tsx
+++ b/web/src/components/NewSession.tsx
@@ -1,10 +1,15 @@
-import { useCallback, useEffect, useMemo, useRef, useState } from 'react'
+import { useCallback, useEffect, useMemo, useRef, useState, type KeyboardEvent as ReactKeyboardEvent } from 'react'
 import type { ApiClient } from '@/api/client'
 import type { Machine } from '@/types/api'
+import { Autocomplete } from '@/components/ChatInput/Autocomplete'
+import { FloatingOverlay } from '@/components/ChatInput/FloatingOverlay'
 import { Button } from '@/components/ui/button'
 import { Spinner } from '@/components/Spinner'
 import { usePlatform } from '@/hooks/usePlatform'
 import { useSpawnSession } from '@/hooks/mutations/useSpawnSession'
+import { useSessions } from '@/hooks/queries/useSessions'
+import { useActiveSuggestions, type Suggestion } from '@/hooks/useActiveSuggestions'
+import { useDirectorySuggestions } from '@/hooks/useDirectorySuggestions'
 import { useRecentPaths } from '@/hooks/useRecentPaths'
 
 type AgentType = 'claude' | 'codex' | 'gemini'
@@ -25,11 +30,15 @@ export function NewSession(props: {
 }) {
     const { haptic } = usePlatform()
     const { spawnSession, isPending, error: spawnError } = useSpawnSession(props.api)
+    const { sessions } = useSessions(props.api)
     const isFormDisabled = isPending || props.isLoading
     const { getRecentPaths, addRecentPath, getLastUsedMachineId, setLastUsedMachineId } = useRecentPaths()
 
     const [machineId, setMachineId] = useState<string | null>(null)
     const [directory, setDirectory] = useState('')
+    const [suppressSuggestions, setSuppressSuggestions] = useState(false)
+    const [isDirectoryFocused, setIsDirectoryFocused] = useState(false)
+    const [pathExistence, setPathExistence] = useState<Record<string, boolean>>({})
     const [agent, setAgent] = useState<AgentType>('claude')
     const [yoloMode, setYoloMode] = useState(false)
     const [sessionType, setSessionType] = useState<SessionType>('simple')
@@ -71,6 +80,61 @@ export function NewSession(props: {
         [getRecentPaths, machineId]
     )
 
+    const allPaths = useDirectorySuggestions(machineId, sessions, recentPaths)
+
+    const pathsToCheck = useMemo(
+        () => Array.from(new Set(allPaths)).slice(0, 1000),
+        [allPaths]
+    )
+
+    useEffect(() => {
+        let cancelled = false
+
+        if (!machineId || pathsToCheck.length === 0) {
+            setPathExistence({})
+            return () => { cancelled = true }
+        }
+
+        void props.api.checkMachinePathsExists(machineId, pathsToCheck)
+            .then((result) => {
+                if (cancelled) return
+                setPathExistence(result.exists ?? {})
+            })
+            .catch(() => {
+                if (cancelled) return
+                setPathExistence({})
+            })
+
+        return () => {
+            cancelled = true
+        }
+    }, [machineId, pathsToCheck, props.api])
+
+    const verifiedPaths = useMemo(
+        () => allPaths.filter((path) => pathExistence[path]),
+        [allPaths, pathExistence]
+    )
+
+    const getSuggestions = useCallback(async (query: string): Promise<Suggestion[]> => {
+        const lowered = query.toLowerCase()
+        return verifiedPaths
+            .filter((path) => path.toLowerCase().includes(lowered))
+            .slice(0, 8)
+            .map((path) => ({
+                key: path,
+                text: path,
+                label: path
+            }))
+    }, [verifiedPaths])
+
+    const activeQuery = (!isDirectoryFocused || suppressSuggestions) ? null : directory
+
+    const [suggestions, selectedIndex, moveUp, moveDown, clearSuggestions] = useActiveSuggestions(
+        activeQuery,
+        getSuggestions,
+        { allowEmptyQuery: true, autoSelectFirst: false }
+    )
+
     const handleMachineChange = useCallback((newMachineId: string) => {
         setMachineId(newMachineId)
         // Auto-fill most recent path for the new machine
@@ -86,6 +150,54 @@ export function NewSession(props: {
         setDirectory(path)
     }, [])
 
+    const handleSuggestionSelect = useCallback((index: number) => {
+        const suggestion = suggestions[index]
+        if (suggestion) {
+            setDirectory(suggestion.text)
+            clearSuggestions()
+            setSuppressSuggestions(true)
+        }
+    }, [suggestions, clearSuggestions])
+
+    const handleDirectoryChange = useCallback((value: string) => {
+        setSuppressSuggestions(false)
+        setDirectory(value)
+    }, [])
+
+    const handleDirectoryFocus = useCallback(() => {
+        setSuppressSuggestions(false)
+        setIsDirectoryFocused(true)
+    }, [])
+
+    const handleDirectoryBlur = useCallback(() => {
+        setIsDirectoryFocused(false)
+    }, [])
+
+    const handleDirectoryKeyDown = useCallback((event: ReactKeyboardEvent<HTMLInputElement>) => {
+        if (suggestions.length === 0) return
+
+        if (event.key === 'ArrowUp') {
+            event.preventDefault()
+            moveUp()
+        }
+
+        if (event.key === 'ArrowDown') {
+            event.preventDefault()
+            moveDown()
+        }
+
+        if (event.key === 'Enter' || event.key === 'Tab') {
+            if (selectedIndex >= 0) {
+                event.preventDefault()
+                handleSuggestionSelect(selectedIndex)
+            }
+        }
+
+        if (event.key === 'Escape') {
+            clearSuggestions()
+        }
+    }, [suggestions, selectedIndex, moveUp, moveDown, clearSuggestions, handleSuggestionSelect])
+
     async function handleCreate() {
         if (!machineId || !directory.trim()) return
 
@@ -152,14 +264,30 @@ export function NewSession(props: {
                 <label className="text-xs font-medium text-[var(--app-hint)]">
                     Directory
                 </label>
-                <input
-                    type="text"
-                    placeholder="/path/to/project"
-                    value={directory}
-                    onChange={(e) => setDirectory(e.target.value)}
-                    disabled={isFormDisabled}
-                    className="w-full rounded-md border border-[var(--app-border)] bg-[var(--app-bg)] p-2 text-sm focus:outline-none focus:ring-2 focus:ring-[var(--app-link)] disabled:opacity-50"
-                />
+                <div className="relative">
+                    <input
+                        type="text"
+                        placeholder="/path/to/project"
+                        value={directory}
+                        onChange={(event) => handleDirectoryChange(event.target.value)}
+                        onKeyDown={handleDirectoryKeyDown}
+                        onFocus={handleDirectoryFocus}
+                        onBlur={handleDirectoryBlur}
+                        disabled={isFormDisabled}
+                        className="w-full rounded-md border border-[var(--app-border)] bg-[var(--app-bg)] p-2 text-sm focus:outline-none focus:ring-2 focus:ring-[var(--app-link)] disabled:opacity-50"
+                    />
+                    {suggestions.length > 0 && (
+                        <div className="absolute top-full left-0 right-0 z-10 mt-1">
+                            <FloatingOverlay maxHeight={200}>
+                                <Autocomplete
+                                    suggestions={suggestions}
+                                    selectedIndex={selectedIndex}
+                                    onSelect={handleSuggestionSelect}
+                                />
+                            </FloatingOverlay>
+                        </div>
+                    )}
+                </div>
 
                 {/* Recent Paths */}
                 {recentPaths.length > 0 && (
diff --git a/web/src/hooks/useActiveSuggestions.ts b/web/src/hooks/useActiveSuggestions.ts
index 60eb33d3..c5dcb521 100644
--- a/web/src/hooks/useActiveSuggestions.ts
+++ b/web/src/hooks/useActiveSuggestions.ts
@@ -1,4 +1,4 @@
-import { useState, useCallback, useEffect, useMemo, useRef } from 'react'
+import { useState, useCallback, useEffect, useRef } from 'react'
 
 export interface Suggestion {
     key: string
@@ -11,6 +11,7 @@ interface SuggestionOptions {
     clampSelection?: boolean   // If true, clamp instead of preserving exact position
     autoSelectFirst?: boolean  // If true, automatically select first item when suggestions appear
     wrapAround?: boolean       // If true, wrap around when reaching top/bottom
+    allowEmptyQuery?: boolean  // If true, allow empty string queries
 }
 
 /**
@@ -71,7 +72,8 @@ export function useActiveSuggestions(
     const {
         clampSelection = true,
         autoSelectFirst = true,
-        wrapAround = true
+        wrapAround = true,
+        allowEmptyQuery = false
     } = options
 
     // State for suggestions
@@ -129,11 +131,13 @@ export function useActiveSuggestions(
     const handlerRef = useRef(handler)
     handlerRef.current = handler
 
-    const sync = useMemo(() => {
-        return new ValueSync<string | null>(async (query) => {
-            if (!query) return
+    const syncRef = useRef<ValueSync<string | null> | null>(null)
 
-            const suggestions = await handlerRef.current(query)
+    useEffect(() => {
+        const sync = new ValueSync<string | null>(async (nextQuery) => {
+            if (nextQuery === null || (!allowEmptyQuery && nextQuery === '')) return
+
+            const suggestions = await handlerRef.current(nextQuery)
 
             setState((prev) => {
                 if (clampSelection) {
@@ -174,18 +178,23 @@ export function useActiveSuggestions(
                 }
             })
         })
-    }, [clampSelection, autoSelectFirst])
+
+        syncRef.current = sync
+
+        return () => {
+            sync.stop()
+            if (syncRef.current === sync) {
+                syncRef.current = null
+            }
+        }
+    }, [clampSelection, autoSelectFirst, allowEmptyQuery])
 
     useEffect(() => {
-        sync.setValue(query)
-    }, [query, sync])
-
-    useEffect(() => {
-        return () => sync.stop()
-    }, [sync])
+        syncRef.current?.setValue(query)
+    }, [query, handler, clampSelection, autoSelectFirst, allowEmptyQuery])
 
     // If no query return empty suggestions
-    if (!query) {
+    if (query === null || (!allowEmptyQuery && query === '')) {
         return [[], -1, moveUp, moveDown, clear] as const
     }
 
diff --git a/web/src/hooks/useDirectorySuggestions.ts b/web/src/hooks/useDirectorySuggestions.ts
new file mode 100644
index 00000000..8aee8844
--- /dev/null
+++ b/web/src/hooks/useDirectorySuggestions.ts
@@ -0,0 +1,31 @@
+import { useMemo } from 'react'
+import type { SessionSummary } from '@/types/api'
+
+export function useDirectorySuggestions(
+    machineId: string | null,
+    sessions: SessionSummary[],
+    recentPaths: string[]
+): string[] {
+    return useMemo(() => {
+        const machineSessions = machineId
+            ? sessions.filter((session) => session.metadata?.machineId === machineId)
+            : sessions
+
+        const sessionPaths = machineSessions
+            .map((session) => session.metadata?.path)
+            .filter((path): path is string => Boolean(path))
+
+        const worktreePaths = machineSessions
+            .map((session) => session.metadata?.worktree?.basePath)
+            .filter((path): path is string => Boolean(path))
+
+        const dedupedRecent = [...new Set(recentPaths)]
+        const recentSet = new Set(dedupedRecent)
+
+        const otherPaths = [...new Set([...sessionPaths, ...worktreePaths])]
+            .filter((path) => !recentSet.has(path))
+            .sort((a, b) => a.localeCompare(b))
+
+        return [...dedupedRecent, ...otherPaths]
+    }, [machineId, sessions, recentPaths])
+}
diff --git a/web/src/types/api.ts b/web/src/types/api.ts
index 8e43eec4..b1af1ed6 100644
--- a/web/src/types/api.ts
+++ b/web/src/types/api.ts
@@ -70,6 +70,7 @@ export type Session = {
 export type SessionSummaryMetadata = {
     name?: string
     path: string
+    machineId?: string
     summary?: { text: string }
     flavor?: string | null
     worktree?: WorktreeMetadata
@@ -132,6 +133,7 @@ export type MessagesResponse = {
 }
 
 export type MachinesResponse = { machines: Machine[] }
+export type MachinePathsExistsResponse = { exists: Record<string, boolean> }
 
 export type SpawnResponse =
     | { type: 'success'; sessionId: string }