fix: detect attachment mime from file contents (#23291)

6 files changed, 198 insertions, 77 deletions

diff --git a/packages/opencode/src/session/message-v2.ts b/packages/opencode/src/session/message-v2.ts
index 46686947e..057b5eb66 100644
--- a/packages/opencode/src/session/message-v2.ts
+++ b/packages/opencode/src/session/message-v2.ts
@@ -11,6 +11,7 @@ import { MessageTable, PartTable, SessionTable } from "./session.sql"
 import { ProviderError } from "@/provider"
 import { iife } from "@/util/iife"
 import { errorMessage } from "@/util/error"
+import { isMedia } from "@/util/media"
 import type { SystemError } from "bun"
 import type { Provider } from "@/provider"
 import { ModelID, ProviderID } from "@/provider/schema"
@@ -25,10 +26,7 @@ interface FetchDecompressionError extends Error {
 }
 
 export const SYNTHETIC_ATTACHMENT_PROMPT = "Attached image(s) from tool result:"
-
-export function isMedia(mime: string) {
-  return mime.startsWith("image/") || mime === "application/pdf"
-}
+export { isMedia }
 
 export const OutputLengthError = NamedError.create("MessageOutputLengthError", z.object({}))
 export const AbortedError = NamedError.create("MessageAbortedError", z.object({ message: z.string() }))
diff --git a/packages/opencode/src/tool/read.ts b/packages/opencode/src/tool/read.ts
index 18c668ca0..29d36692c 100644
--- a/packages/opencode/src/tool/read.ts
+++ b/packages/opencode/src/tool/read.ts
@@ -1,7 +1,6 @@
 import z from "zod"
-import { Effect, Scope } from "effect"
+import { Effect, Option, Scope } from "effect"
 import { createReadStream } from "fs"
-import { open } from "fs/promises"
 import * as path from "path"
 import { createInterface } from "readline"
 import * as Tool from "./tool"
@@ -11,12 +10,14 @@ import DESCRIPTION from "./read.txt"
 import { Instance } from "../project/instance"
 import { assertExternalDirectoryEffect } from "./external-directory"
 import { Instruction } from "../session/instruction"
+import { isImageAttachment, isPdfAttachment, sniffAttachmentMime } from "@/util/media"
 
 const DEFAULT_READ_LIMIT = 2000
 const MAX_LINE_LENGTH = 2000
 const MAX_LINE_SUFFIX = `... (line truncated to ${MAX_LINE_LENGTH} chars)`
 const MAX_BYTES = 50 * 1024
 const MAX_BYTES_LABEL = `${MAX_BYTES / 1024} KB`
+const SAMPLE_BYTES = 4096
 
 const parameters = z.object({
   filePath: z.string().describe("The absolute path to the file or directory to read"),
@@ -77,6 +78,64 @@ export const ReadTool = Tool.define(
       yield* lsp.touchFile(filepath, false).pipe(Effect.ignore, Effect.forkIn(scope))
     })
 
+    const readSample = Effect.fn("ReadTool.readSample")(function* (filepath: string, fileSize: number, sampleSize: number) {
+      if (fileSize === 0) return new Uint8Array()
+
+      return yield* Effect.scoped(
+        Effect.gen(function* () {
+          const file = yield* fs.open(filepath, { flag: "r" })
+          return Option.getOrElse(yield* file.readAlloc(Math.min(sampleSize, fileSize)), () => new Uint8Array())
+        }),
+      )
+    })
+
+    const isBinaryFile = (filepath: string, bytes: Uint8Array) => {
+      const ext = path.extname(filepath).toLowerCase()
+      switch (ext) {
+        case ".zip":
+        case ".tar":
+        case ".gz":
+        case ".exe":
+        case ".dll":
+        case ".so":
+        case ".class":
+        case ".jar":
+        case ".war":
+        case ".7z":
+        case ".doc":
+        case ".docx":
+        case ".xls":
+        case ".xlsx":
+        case ".ppt":
+        case ".pptx":
+        case ".odt":
+        case ".ods":
+        case ".odp":
+        case ".bin":
+        case ".dat":
+        case ".obj":
+        case ".o":
+        case ".a":
+        case ".lib":
+        case ".wasm":
+        case ".pyc":
+        case ".pyo":
+          return true
+      }
+
+      if (bytes.length === 0) return false
+
+      let nonPrintableCount = 0
+      for (let i = 0; i < bytes.length; i++) {
+        if (bytes[i] === 0) return true
+        if (bytes[i] < 9 || (bytes[i] > 13 && bytes[i] < 32)) {
+          nonPrintableCount++
+        }
+      }
+
+      return nonPrintableCount / bytes.length > 0.3
+    }
+
     const run = Effect.fn("ReadTool.execute")(function* (params: z.infer<typeof parameters>, ctx: Tool.Context) {
       if (params.offset !== undefined && params.offset < 1) {
         return yield* Effect.fail(new Error("offset must be greater than or equal to 1"))
@@ -141,12 +200,12 @@ export const ReadTool = Tool.define(
       }
 
       const loaded = yield* instruction.resolve(ctx.messages, filepath, ctx.messageID)
+      const sample = yield* readSample(filepath, Number(stat.size), SAMPLE_BYTES)
 
-      const mime = AppFileSystem.mimeType(filepath)
-      const isImage = mime.startsWith("image/") && mime !== "image/svg+xml" && mime !== "image/vnd.fastbidsheet"
-      const isPdf = mime === "application/pdf"
-      if (isImage || isPdf) {
-        const msg = `${isImage ? "Image" : "PDF"} read successfully`
+      const mime = sniffAttachmentMime(sample, AppFileSystem.mimeType(filepath))
+      if (isImageAttachment(mime) || isPdfAttachment(mime)) {
+        const bytes = yield* fs.readFile(filepath)
+        const msg = isPdfAttachment(mime) ? "PDF read successfully" : "Image read successfully"
         return {
           title,
           output: msg,
@@ -159,13 +218,13 @@ export const ReadTool = Tool.define(
             {
               type: "file" as const,
               mime,
-              url: `data:${mime};base64,${Buffer.from(yield* fs.readFile(filepath)).toString("base64")}`,
+              url: `data:${mime};base64,${Buffer.from(bytes).toString("base64")}`,
             },
           ],
         }
       }
 
-      if (yield* Effect.promise(() => isBinaryFile(filepath, Number(stat.size)))) {
+      if (isBinaryFile(filepath, sample)) {
         return yield* Effect.fail(new Error(`Cannot read binary file: ${filepath}`))
       }
 
@@ -261,63 +320,3 @@ async function lines(filepath: string, opts: { limit: number; offset: number })
 
   return { raw, count, cut, more, offset: opts.offset }
 }
-
-async function isBinaryFile(filepath: string, fileSize: number): Promise<boolean> {
-  const ext = path.extname(filepath).toLowerCase()
-  // binary check for common non-text extensions
-  switch (ext) {
-    case ".zip":
-    case ".tar":
-    case ".gz":
-    case ".exe":
-    case ".dll":
-    case ".so":
-    case ".class":
-    case ".jar":
-    case ".war":
-    case ".7z":
-    case ".doc":
-    case ".docx":
-    case ".xls":
-    case ".xlsx":
-    case ".ppt":
-    case ".pptx":
-    case ".odt":
-    case ".ods":
-    case ".odp":
-    case ".bin":
-    case ".dat":
-    case ".obj":
-    case ".o":
-    case ".a":
-    case ".lib":
-    case ".wasm":
-    case ".pyc":
-    case ".pyo":
-      return true
-    default:
-      break
-  }
-
-  if (fileSize === 0) return false
-
-  const fh = await open(filepath, "r")
-  try {
-    const sampleSize = Math.min(4096, fileSize)
-    const bytes = Buffer.alloc(sampleSize)
-    const result = await fh.read(bytes, 0, sampleSize, 0)
-    if (result.bytesRead === 0) return false
-
-    let nonPrintableCount = 0
-    for (let i = 0; i < result.bytesRead; i++) {
-      if (bytes[i] === 0) return true
-      if (bytes[i] < 9 || (bytes[i] > 13 && bytes[i] < 32)) {
-        nonPrintableCount++
-      }
-    }
-    // If >30% non-printable characters, consider it binary
-    return nonPrintableCount / result.bytesRead > 0.3
-  } finally {
-    await fh.close()
-  }
-}
diff --git a/packages/opencode/src/tool/webfetch.ts b/packages/opencode/src/tool/webfetch.ts
index 6498b871f..1d988b8d4 100644
--- a/packages/opencode/src/tool/webfetch.ts
+++ b/packages/opencode/src/tool/webfetch.ts
@@ -4,6 +4,7 @@ import { HttpClient, HttpClientRequest } from "effect/unstable/http"
 import * as Tool from "./tool"
 import TurndownService from "turndown"
 import DESCRIPTION from "./webfetch.txt"
+import { isImageAttachment } from "@/util/media"
 
 const MAX_RESPONSE_SIZE = 5 * 1024 * 1024 // 5MB
 const DEFAULT_TIMEOUT = 30 * 1000 // 30 seconds
@@ -104,10 +105,7 @@ export const WebFetchTool = Tool.define(
           const mime = contentType.split(";")[0]?.trim().toLowerCase() || ""
           const title = `${params.url} (${contentType})`
 
-          // Check if response is an image
-          const isImage = mime.startsWith("image/") && mime !== "image/svg+xml" && mime !== "image/vnd.fastbidsheet"
-
-          if (isImage) {
+          if (isImageAttachment(mime)) {
             const base64Content = Buffer.from(arrayBuffer).toString("base64")
             return {
               title,
diff --git a/packages/opencode/src/util/media.ts b/packages/opencode/src/util/media.ts
new file mode 100644
index 000000000..0e98f53a5
--- /dev/null
+++ b/packages/opencode/src/util/media.ts
@@ -0,0 +1,29 @@
+const startsWith = (bytes: Uint8Array, prefix: number[]) => prefix.every((value, index) => bytes[index] === value)
+
+export function isPdfAttachment(mime: string) {
+  return mime === "application/pdf"
+}
+
+export function isMedia(mime: string) {
+  return mime.startsWith("image/") || isPdfAttachment(mime)
+}
+
+export function isImageAttachment(mime: string) {
+  return mime.startsWith("image/") && mime !== "image/svg+xml" && mime !== "image/vnd.fastbidsheet"
+}
+
+export function sniffAttachmentMime(bytes: Uint8Array, fallback: string) {
+  if (startsWith(bytes, [0x89, 0x50, 0x4e, 0x47, 0x0d, 0x0a, 0x1a, 0x0a])) return "image/png"
+  if (startsWith(bytes, [0xff, 0xd8, 0xff])) return "image/jpeg"
+  if (startsWith(bytes, [0x47, 0x49, 0x46, 0x38])) return "image/gif"
+  if (startsWith(bytes, [0x42, 0x4d])) return "image/bmp"
+  if (startsWith(bytes, [0x25, 0x50, 0x44, 0x46, 0x2d])) return "application/pdf"
+  if (
+    startsWith(bytes, [0x52, 0x49, 0x46, 0x46]) &&
+    startsWith(bytes.subarray(8), [0x57, 0x45, 0x42, 0x50])
+  ) {
+    return "image/webp"
+  }
+
+  return fallback
+}
diff --git a/packages/opencode/test/session/message-v2.test.ts b/packages/opencode/test/session/message-v2.test.ts
index 6d4e994a8..55ae65c56 100644
--- a/packages/opencode/test/session/message-v2.test.ts
+++ b/packages/opencode/test/session/message-v2.test.ts
@@ -1,6 +1,7 @@
 import { describe, expect, test } from "bun:test"
 import { APICallError } from "ai"
 import { MessageV2 } from "../../src/session/message-v2"
+import { ProviderTransform } from "../../src/provider"
 import type { Provider } from "../../src/provider"
 import { ModelID, ProviderID } from "../../src/provider/schema"
 import { SessionID, MessageID, PartID } from "../../src/session/schema"
@@ -359,6 +360,89 @@ describe("session.message-v2.toModelMessage", () => {
     ])
   })
 
+  test("preserves jpeg tool-result media for anthropic models", async () => {
+    const anthropicModel: Provider.Model = {
+      ...model,
+      id: ModelID.make("anthropic/claude-opus-4-7"),
+      providerID: ProviderID.make("anthropic"),
+      api: {
+        id: "claude-opus-4-7-20250805",
+        url: "https://api.anthropic.com",
+        npm: "@ai-sdk/anthropic",
+      },
+      capabilities: {
+        ...model.capabilities,
+        attachment: true,
+        input: {
+          ...model.capabilities.input,
+          image: true,
+          pdf: true,
+        },
+      },
+    }
+    const jpeg = Buffer.from([0xff, 0xd8, 0xff, 0xe0, 0x00, 0x10, 0x4a, 0x46, 0x49, 0x46, 0x00, 0x01]).toString(
+      "base64",
+    )
+    const userID = "m-user-anthropic"
+    const assistantID = "m-assistant-anthropic"
+    const input: MessageV2.WithParts[] = [
+      {
+        info: userInfo(userID),
+        parts: [
+          {
+            ...basePart(userID, "u1-anthropic"),
+            type: "text",
+            text: "run tool",
+          },
+        ] as MessageV2.Part[],
+      },
+      {
+        info: assistantInfo(assistantID, userID),
+        parts: [
+          {
+            ...basePart(assistantID, "a1-anthropic"),
+            type: "tool",
+            callID: "call-anthropic-1",
+            tool: "read",
+            state: {
+              status: "completed",
+              input: { filePath: "/tmp/rails-demo.png" },
+              output: "Image read successfully",
+              title: "Read",
+              metadata: {},
+              time: { start: 0, end: 1 },
+              attachments: [
+                {
+                  ...basePart(assistantID, "file-anthropic-1"),
+                  type: "file",
+                  mime: "image/jpeg",
+                  filename: "rails-demo.png",
+                  url: `data:image/jpeg;base64,${jpeg}`,
+                },
+              ],
+            },
+          },
+        ] as MessageV2.Part[],
+      },
+    ]
+
+    const result = ProviderTransform.message(await MessageV2.toModelMessages(input, anthropicModel), anthropicModel, {})
+    expect(result).toHaveLength(3)
+    expect(result[2].role).toBe("tool")
+    expect(result[2].content[0]).toMatchObject({
+      type: "tool-result",
+      toolCallId: "call-anthropic-1",
+      toolName: "read",
+      output: {
+        type: "content",
+        value: [
+          { type: "text", text: "Image read successfully" },
+          { type: "media", mediaType: "image/jpeg", data: jpeg },
+        ],
+      },
+    })
+  })
+
   test("omits provider metadata when assistant model differs", async () => {
     const userID = "m-user"
     const assistantID = "m-assistant"
diff --git a/packages/opencode/test/tool/read.test.ts b/packages/opencode/test/tool/read.test.ts
index 7456990ad..42817d15d 100644
--- a/packages/opencode/test/tool/read.test.ts
+++ b/packages/opencode/test/tool/read.test.ts
@@ -394,6 +394,19 @@ describe("tool.read truncation", () => {
     }),
   )
 
+  it.live("detects attachment media from file contents", () =>
+    Effect.gen(function* () {
+      const dir = yield* tmpdirScoped()
+      const jpeg = Buffer.from([0xff, 0xd8, 0xff, 0xe0, 0x00, 0x10, 0x4a, 0x46, 0x49, 0x46, 0x00, 0x01])
+      yield* put(path.join(dir, "image.bin"), jpeg)
+
+      const result = yield* exec(dir, { filePath: path.join(dir, "image.bin") })
+      expect(result.output).toBe("Image read successfully")
+      expect(result.attachments?.[0].mime).toBe("image/jpeg")
+      expect(result.attachments?.[0].url.startsWith("data:image/jpeg;base64,")).toBe(true)
+    }),
+  )
+
   it.live("large image files are properly attached without error", () =>
     Effect.gen(function* () {
       const result = yield* exec(FIXTURES_DIR, { filePath: path.join(FIXTURES_DIR, "large-image.png") })