diff --git a/src/cli/config-manager/add-plugin-to-opencode-config.ts b/src/cli/config-manager/add-plugin-to-opencode-config.ts
index 23c398873..8cb7d0838 100644
--- a/src/cli/config-manager/add-plugin-to-opencode-config.ts
+++ b/src/cli/config-manager/add-plugin-to-opencode-config.ts
@@ -79,11 +79,7 @@ export async function addPluginToOpenCodeConfig(currentVersion: string): Promise
 
     const normalizedPlugins = [...otherPlugins]
 
-    if (canonicalEntries.length > 0 || legacyEntries.length > 0) {
-      normalizedPlugins.push(pluginEntry)
-    } else {
-      normalizedPlugins.push(pluginEntry)
-    }
+    normalizedPlugins.push(pluginEntry)
 
     config.plugin = normalizedPlugins
 
diff --git a/src/cli/config-manager/parse-opencode-config-file.test.ts b/src/cli/config-manager/parse-opencode-config-file.test.ts
new file mode 100644
index 000000000..f8351d8c2
--- /dev/null
+++ b/src/cli/config-manager/parse-opencode-config-file.test.ts
@@ -0,0 +1,49 @@
+import { afterEach, describe, expect, test } from "bun:test"
+import { mkdtempSync, rmSync, writeFileSync } from "node:fs"
+import { tmpdir } from "node:os"
+import { join } from "node:path"
+
+import { parseOpenCodeConfigFileWithError } from "./parse-opencode-config-file"
+
+describe("parseOpenCodeConfigFileWithError", () => {
+  const tempDirectories: string[] = []
+
+  afterEach(() => {
+    for (const directory of tempDirectories.splice(0)) {
+      rmSync(directory, { recursive: true, force: true })
+    }
+  })
+
+  test("#given a valid object config #when parsing the file #then it returns the parsed config", () => {
+    // given
+    const directory = mkdtempSync(join(tmpdir(), "omo-parse-config-"))
+    tempDirectories.push(directory)
+    const filePath = join(directory, "opencode.json")
+    writeFileSync(filePath, '{"plugin": ["oh-my-openagent"]}\n', "utf-8")
+
+    // when
+    const result = parseOpenCodeConfigFileWithError(filePath)
+
+    // then
+    expect(result).toEqual({
+      config: { plugin: ["oh-my-openagent"] },
+    })
+  })
+
+  test("#given a null config payload #when parsing the file #then it returns a null parse error", () => {
+    // given
+    const directory = mkdtempSync(join(tmpdir(), "omo-parse-config-"))
+    tempDirectories.push(directory)
+    const filePath = join(directory, "opencode.json")
+    writeFileSync(filePath, "null\n", "utf-8")
+
+    // when
+    const result = parseOpenCodeConfigFileWithError(filePath)
+
+    // then
+    expect(result).toEqual({
+      config: null,
+      error: `Config file parsed to null/undefined: ${filePath}. Ensure it contains valid JSON.`,
+    })
+  })
+})
diff --git a/src/cli/config-manager/parse-opencode-config-file.ts b/src/cli/config-manager/parse-opencode-config-file.ts
index 3e399d847..ed1f25526 100644
--- a/src/cli/config-manager/parse-opencode-config-file.ts
+++ b/src/cli/config-manager/parse-opencode-config-file.ts
@@ -30,7 +30,7 @@ export function parseOpenCodeConfigFileWithError(path: string): ParseConfigResul
 
     const config = parseJsonc<OpenCodeConfig>(content)
 
-    if (config === null || config === undefined) {
+    if (config == null) {
       return { config: null, error: `Config file parsed to null/undefined: ${path}. Ensure it contains valid JSON.` }
     }