diff --git a/packages/opencode/src/util/log.ts b/packages/opencode/src/util/log.ts
index 6941310bbbd..483d9a337dc 100644
--- a/packages/opencode/src/util/log.ts
+++ b/packages/opencode/src/util/log.ts
@@ -57,7 +57,6 @@ export namespace Log {
 
   export async function init(options: Options) {
     if (options.level) level = options.level
-    cleanup(Global.Path.log)
     if (options.print) return
     logpath = path.join(
       Global.Path.log,
@@ -71,6 +70,7 @@ export namespace Log {
       writer.flush()
       return num
     }
+    cleanup(Global.Path.log)
   }
 
   async function cleanup(dir: string) {
diff --git a/packages/opencode/test/util/log.test.ts b/packages/opencode/test/util/log.test.ts
new file mode 100644
index 00000000000..6878ec674c5
--- /dev/null
+++ b/packages/opencode/test/util/log.test.ts
@@ -0,0 +1,68 @@
+import { test, expect } from "bun:test"
+import { Log } from "@/util/log"
+import fs from "fs/promises"
+import path from "path"
+import * as Global from "@/global"
+
+describe("Log", () => {
+  const testLogDir = path.join(process.cwd(), ".test-log")
+  const logDir = path.join(testLogDir, "share", "opencode", "log")
+
+  test("should not delete existing log file when reinitializing with DEBUG", async () => {
+    await fs.mkdir(testLogDir, { recursive: true })
+    await fs.mkdir(logDir, { recursive: true })
+
+    await Log.init({ print: true })
+    const initialLogPath = Log.file()
+    expect(initialLogPath).toBeTruthy()
+    expect(initialLogPath).toContain(logDir)
+
+    const initialContent = "Initial log content\n"
+    await fs.appendFile(initialLogPath, initialContent)
+
+    await Log.init({ print: true, level: "DEBUG" })
+    const debugLogPath = Log.file()
+
+    const initialExists = await fs
+      .access(initialLogPath)
+      .then(() => true)
+      .catch(() => false)
+    expect(initialExists).toBe(true)
+
+    const initialFileContent = await fs.readFile(initialLogPath, "utf-8")
+    expect(initialFileContent).toContain(initialContent)
+
+    expect(debugLogPath).toBeTruthy()
+    expect(debugLogPath).not.toBe(initialLogPath)
+
+    await fs.rm(testLogDir, { recursive: true, force: true })
+  })
+
+  test("should maintain log rotation when reinitializing with DEBUG", async () => {
+    await fs.mkdir(testLogDir, { recursive: true })
+    await fs.mkdir(logDir, { recursive: true })
+
+    const oldFiles: string[] = []
+    for (let i = 0; i < 15; i++) {
+      const timestamp = new Date(Date.now() - i * 1000 * 60 * 60 * 24)
+      const filename = timestamp.toISOString().split(".")[0].replace(/:/g, "") + ".log"
+      const filepath = path.join(logDir, filename)
+      await fs.writeFile(filepath, `Old log ${i}\n`)
+      oldFiles.push(filepath)
+    }
+
+    await Log.init({ print: true, level: "DEBUG" })
+
+    const allFiles = (await fs.readdir(logDir)).sort()
+    expect(allFiles.length).toBeLessThanOrEqual(10)
+
+    const currentLogPath = Log.file()
+    const currentExists = await fs
+      .access(currentLogPath)
+      .then(() => true)
+      .catch(() => false)
+    expect(currentExists).toBe(true)
+
+    await fs.rm(testLogDir, { recursive: true, force: true })
+  })
+})