diff --git a/src/services/user-memory-learning.ts b/src/services/user-memory-learning.ts
index eebbe62..df8c206 100644
--- a/src/services/user-memory-learning.ts
+++ b/src/services/user-memory-learning.ts
@@ -632,6 +632,7 @@ async function analyzeUserProfile(
   existingProfile: UserProfile | null
 ): Promise<AnalysisResult | null> {
   log("user-profile-learning: analyze called", { hasProfile: !!existingProfile });
+  let opencodeProviderError: unknown;
   if (CONFIG.opencodeProvider && CONFIG.opencodeModel) {
     log("user-profile-learning: trying opencode provider");
     try {
@@ -694,6 +695,7 @@ Use the update_user_profile tool to save the ${existingProfile ? "updated" : "ne
       }
       return { raw: rawData, merged: null };
     } catch (e) {
+      opencodeProviderError = e;
       log("user-profile-learning: opencode provider failed, falling back to external API", {
         error: String(e),
       });
@@ -701,6 +703,9 @@ Use the update_user_profile tool to save the ${existingProfile ? "updated" : "ne
   }
 
   if (!CONFIG.memoryModel || !CONFIG.memoryApiUrl) {
+    if (opencodeProviderError) {
+      throw opencodeProviderError;
+    }
     log("User Profile Config Check Failed:", {
       memoryModel: CONFIG.memoryModel,
       memoryApiUrl: CONFIG.memoryApiUrl,
diff --git a/tests/user-profile-learning-error.test.ts b/tests/user-profile-learning-error.test.ts
new file mode 100644
index 0000000..1c020eb
--- /dev/null
+++ b/tests/user-profile-learning-error.test.ts
@@ -0,0 +1,155 @@
+import { afterEach, describe, expect, it } from "bun:test";
+import { mkdtempSync, rmSync, writeFileSync } from "node:fs";
+import { tmpdir } from "node:os";
+import { join } from "node:path";
+
+const tempDirs: string[] = [];
+
+const learningUrl = new URL(
+  "../src/services/user-memory-learning.js",
+  import.meta.url
+).href;
+const configUrl = new URL("../src/config.js", import.meta.url).href;
+const tagsUrl = new URL("../src/services/tags.js", import.meta.url).href;
+const promptManagerUrl = new URL(
+  "../src/services/user-prompt/user-prompt-manager.js",
+  import.meta.url
+).href;
+const profileManagerUrl = new URL(
+  "../src/services/user-profile/user-profile-manager.js",
+  import.meta.url
+).href;
+const opencodeProviderLoaderUrl = new URL(
+  "../src/services/ai/opencode-provider-loader.js",
+  import.meta.url
+).href;
+const profileLlmClientUrl = new URL(
+  "../src/services/ai/profile-llm-client.js",
+  import.meta.url
+).href;
+const loggerUrl = new URL("../src/services/logger.js", import.meta.url).href;
+
+function runProviderFailureScenario() {
+  const dir = mkdtempSync(join(tmpdir(), "opencode-mem-profile-error-"));
+  tempDirs.push(dir);
+  const scriptPath = join(dir, "scenario.mjs");
+  const script = `
+import { mock } from "bun:test";
+
+const prompts = Array.from({ length: 10 }, (_, i) => ({
+  id: \`prompt-\${i}\`,
+  sessionId: "session-1",
+  messageId: \`msg-\${i}\`,
+  projectPath: "/workspace",
+  content: \`Implement feature \${i}\`,
+  createdAt: i + 1,
+  captured: false,
+  user_learning_captured: false,
+  capture_attempts: 0,
+}));
+
+mock.module(${JSON.stringify(configUrl)}, () => ({
+  CONFIG: {
+    autoCaptureProviderStatus: { ready: true, mode: "opencode", issues: [] },
+    userProfileAnalysisInterval: 5,
+    opencodeProvider: "opencode-go",
+    opencodeModel: "deepseek-v4-flash",
+    showUserProfileToasts: false,
+  },
+}));
+
+mock.module(${JSON.stringify(tagsUrl)}, () => ({
+  getTags: () => ({
+    user: {
+      tag: "opencode_user_test",
+      displayName: "Test User",
+      userName: "tester",
+      userEmail: "test@example.com",
+    },
+  }),
+}));
+
+mock.module(${JSON.stringify(promptManagerUrl)}, () => ({
+  userPromptManager: {
+    countUnanalyzedForUserLearning: async () => 10,
+    getPromptsForUserLearning: async () => prompts,
+    markMultipleAsUserLearningCaptured: async () => {},
+  },
+}));
+
+mock.module(${JSON.stringify(profileManagerUrl)}, () => ({
+  userProfileManager: {
+    getActiveProfile: async () => null,
+    createProfile: async () => ({}),
+    mergeProfileData: async () => ({}),
+    updateProfile: async () => true,
+    decayInMemory: (d) => ({ data: d }),
+    syncConfidence: () => {},
+  },
+}));
+
+mock.module(${JSON.stringify(loggerUrl)}, () => ({ log: () => {} }));
+
+mock.module(${JSON.stringify(opencodeProviderLoaderUrl)}, () => ({
+  loadOpencodeProvider: async () => ({
+    generateStructuredOutput: async () => {
+      throw new Error(
+        "opencode-mem: opencode reported APIError: Thinking mode does not support this tool_choice"
+      );
+    },
+  }),
+}));
+
+mock.module(${JSON.stringify(profileLlmClientUrl)}, () => ({
+  getOpenCodeClient: async () => ({}),
+}));
+
+try {
+  const { performUserProfileLearning } = await import(${JSON.stringify(learningUrl)});
+  await performUserProfileLearning({}, "/workspace");
+  console.log(JSON.stringify({ error: null }));
+} catch (e) {
+  console.log(JSON.stringify({ error: e?.message ?? String(e) }));
+}
+process.exit(0);
+`;
+
+  writeFileSync(scriptPath, script, "utf-8");
+  const result = Bun.spawnSync({
+    cmd: [process.execPath, scriptPath],
+    stdout: "pipe",
+    stderr: "pipe",
+  });
+  const stdout = Buffer.from(result.stdout).toString("utf8").trim();
+  const stderr = Buffer.from(result.stderr).toString("utf8").trim();
+  const jsonLine = stdout
+    .split("\n")
+    .reverse()
+    .find((line) => line.trim().startsWith("{"));
+
+  return {
+    exitCode: result.exitCode,
+    stderr,
+    parsed: jsonLine ? JSON.parse(jsonLine) : null,
+  };
+}
+
+afterEach(() => {
+  while (tempDirs.length > 0) {
+    const dir = tempDirs.pop();
+    if (dir) rmSync(dir, { recursive: true, force: true });
+  }
+});
+
+describe("user profile learning error propagation (#265)", () => {
+  it("preserves the opencode provider error when no manual fallback is configured", () => {
+    const result = runProviderFailureScenario();
+
+    expect(result.exitCode).toBe(0);
+    expect(result.stderr).toBe("");
+    expect(result.parsed?.error).toContain("Thinking mode does not support");
+    expect(result.parsed?.error).not.toContain(
+      "External API not configured"
+    );
+  });
+});