diff --git a/cli/src/commands/run/app/_strategies/streaming-structured.ts b/cli/src/commands/run/app/_strategies/streaming-structured.ts
index 2089762d8d..b85db1d808 100644
--- a/cli/src/commands/run/app/_strategies/streaming-structured.ts
+++ b/cli/src/commands/run/app/_strategies/streaming-structured.ts
@@ -1,6 +1,7 @@
 import type { SseEvent } from '../../../../http/sse.js'
 import type { RunContext, RunStrategy } from './index.js'
 import { buildRunBody } from '../../../../api/app-run.js'
+import { colorEnabled, colorScheme } from '../../../../io/color.js'
 import { startSpinner } from '../../../../io/spinner.js'
 import { extractThinkBlocks, stripThinkBlocks } from '../../../../io/think-filter.js'
 import { chatConversationHint, newAppRunObject, RUN_MODES } from '../handlers.js'
@@ -89,7 +90,8 @@ export class StreamingStructuredStrategy implements RunStrategy {
     const respMode = typeof processedResp.mode === 'string' && processedResp.mode !== '' ? processedResp.mode : mode
     deps.io.out.write(printFlags.toPrinter(format).print(newAppRunObject(respMode, processedResp)))
     if (isText && CHAT_MODES.has(respMode)) {
-      const hint = chatConversationHint(processedResp)
+      const cs = colorScheme(colorEnabled(deps.io.isErrTTY))
+      const hint = chatConversationHint(processedResp, cs)
       if (hint !== undefined)
         deps.io.err.write(hint)
     }
diff --git a/cli/src/commands/run/app/_strategies/streaming-text.ts b/cli/src/commands/run/app/_strategies/streaming-text.ts
index 3a23e14791..6a5405a918 100644
--- a/cli/src/commands/run/app/_strategies/streaming-text.ts
+++ b/cli/src/commands/run/app/_strategies/streaming-text.ts
@@ -26,7 +26,7 @@ export class StreamingTextStrategy implements RunStrategy {
 
     try {
       const events = await ctx.runClient.runStream(opts.appId, body, { signal: ctrl.signal })
-      const sp = printFlags.toStreamPrinter(mode, ctx.think)
+      const sp = printFlags.toStreamPrinter(mode, ctx.think, deps.io.isErrTTY)
       const dec = new TextDecoder()
       for await (const ev of events) {
         if (ev.name === 'ping')
diff --git a/cli/src/commands/run/app/file-flags.test.ts b/cli/src/commands/run/app/file-flags.test.ts
index 8f0216a6f0..87babdedec 100644
--- a/cli/src/commands/run/app/file-flags.test.ts
+++ b/cli/src/commands/run/app/file-flags.test.ts
@@ -62,8 +62,8 @@ describe('difyFileType', () => {
     expect(difyFileType('notes.md')).toBe('document')
   })
 
-  it('returns custom for unknown extension', () => {
-    expect(difyFileType('data.xyz')).toBe('custom')
+  it('returns document for unknown extension', () => {
+    expect(difyFileType('data.xyz')).toBe('document')
   })
 
   it('returns custom for no extension', () => {
diff --git a/cli/src/commands/run/app/handlers.ts b/cli/src/commands/run/app/handlers.ts
index 2d040246b4..2cc11b026c 100644
--- a/cli/src/commands/run/app/handlers.ts
+++ b/cli/src/commands/run/app/handlers.ts
@@ -1,3 +1,4 @@
+import type { ColorScheme } from '../../../io/color.js'
 import type { TextHandler } from '../../../printers/format-text.js'
 
 export const RUN_MODES = {
@@ -59,11 +60,11 @@ export const workflowTextHandler: TextHandler = {
   },
 }
 
-export function chatConversationHint(resp: Record<string, unknown>): string | undefined {
+export function chatConversationHint(resp: Record<string, unknown>, cs: ColorScheme): string | undefined {
   const cid = pickString(resp, 'conversation_id')
   if (cid === undefined || cid === '')
     return undefined
-  return `hint: continue this conversation with --conversation ${cid}\n`
+  return `${cs.magenta('hint:')} continue this conversation with --conversation ${cs.cyan(cid)}\n`
 }
 
 function pickString(o: Record<string, unknown>, key: string): string | undefined {
diff --git a/cli/src/commands/run/app/print-flags.ts b/cli/src/commands/run/app/print-flags.ts
index 8001bc6fc5..a90d7b8f8c 100644
--- a/cli/src/commands/run/app/print-flags.ts
+++ b/cli/src/commands/run/app/print-flags.ts
@@ -21,7 +21,7 @@ export class AppRunPrintFlags extends CompositePrintFlags {
     return [this.jsonYaml, this.text]
   }
 
-  toStreamPrinter(mode: string, think = false): StreamPrinter {
-    return streamPrinterFor(mode, think)
+  toStreamPrinter(mode: string, think = false, isTTY = false): StreamPrinter {
+    return streamPrinterFor(mode, think, isTTY)
   }
 }
diff --git a/cli/src/commands/run/app/stream-handlers.ts b/cli/src/commands/run/app/stream-handlers.ts
index 64d21ea3f2..a54dbfe54b 100644
--- a/cli/src/commands/run/app/stream-handlers.ts
+++ b/cli/src/commands/run/app/stream-handlers.ts
@@ -3,6 +3,7 @@ import type { StreamPrinter } from '../../../printers/stream-printer.js'
 import type { HitlPausePayload } from './sse-collector.js'
 import { newError } from '../../../errors/base.js'
 import { ErrorCode } from '../../../errors/codes.js'
+import { colorEnabled, colorScheme } from '../../../io/color.js'
 import { ThinkChunkFilter } from '../../../io/think-filter.js'
 import { RUN_MODES } from './handlers.js'
 import { HitlPauseError } from './sse-collector.js'
@@ -42,8 +43,10 @@ function handleCommonEvents(ev: SseEvent): boolean {
 class ChatStreamPrinter implements StreamPrinter {
   private convoId = ''
   private readonly filter: ThinkChunkFilter
-  constructor(think: boolean) {
+  private readonly isTTY: boolean
+  constructor(think: boolean, isTTY = false) {
     this.filter = new ThinkChunkFilter(think)
+    this.isTTY = isTTY
   }
 
   onEvent(out: NodeJS.WritableStream, errOut: NodeJS.WritableStream, ev: SseEvent): void {
@@ -72,8 +75,10 @@ class ChatStreamPrinter implements StreamPrinter {
   onEnd(out: NodeJS.WritableStream, errOut: NodeJS.WritableStream): void {
     this.filter.flush(out, errOut)
     out.write('\n')
-    if (this.convoId !== '')
-      errOut.write(`hint: continue this conversation with --conversation ${this.convoId}\n`)
+    if (this.convoId !== '') {
+      const cs = colorScheme(colorEnabled(this.isTTY))
+      errOut.write(`${cs.magenta('hint:')} continue this conversation with --conversation ${cs.cyan(this.convoId)}\n`)
+    }
   }
 }
 
@@ -139,17 +144,17 @@ class WorkflowStreamPrinter implements StreamPrinter {
   }
 }
 
-const FACTORIES: Record<string, (think: boolean) => StreamPrinter> = {
-  [RUN_MODES.Chat]: think => new ChatStreamPrinter(think),
-  [RUN_MODES.AdvancedChat]: think => new ChatStreamPrinter(think),
-  [RUN_MODES.AgentChat]: think => new ChatStreamPrinter(think),
-  [RUN_MODES.Completion]: think => new CompletionStreamPrinter(think),
-  [RUN_MODES.Workflow]: _think => new WorkflowStreamPrinter(),
+const FACTORIES: Record<string, (think: boolean, isTTY: boolean) => StreamPrinter> = {
+  [RUN_MODES.Chat]: (think, isTTY) => new ChatStreamPrinter(think, isTTY),
+  [RUN_MODES.AdvancedChat]: (think, isTTY) => new ChatStreamPrinter(think, isTTY),
+  [RUN_MODES.AgentChat]: (think, isTTY) => new ChatStreamPrinter(think, isTTY),
+  [RUN_MODES.Completion]: (think, _isTTY) => new CompletionStreamPrinter(think),
+  [RUN_MODES.Workflow]: (_think, _isTTY) => new WorkflowStreamPrinter(),
 }
 
-export function streamPrinterFor(mode: string, think = false): StreamPrinter {
+export function streamPrinterFor(mode: string, think = false, isTTY = false): StreamPrinter {
   const f = FACTORIES[mode]
   if (f === undefined)
     throw newError(ErrorCode.Unknown, `unsupported streaming mode "${mode}"`)
-  return f(think)
+  return f(think, isTTY)
 }