diff --git a/src/api/providers/fetchers/__tests__/roo.spec.ts b/src/api/providers/fetchers/__tests__/roo.spec.ts
index 0ee7d8e3ed8..cd86be0b692 100644
--- a/src/api/providers/fetchers/__tests__/roo.spec.ts
+++ b/src/api/providers/fetchers/__tests__/roo.spec.ts
@@ -1,5 +1,6 @@
 import { describe, it, expect, vi, beforeEach, afterEach } from "vitest"
 import { getRooModels } from "../roo"
+import { Package } from "../../../../shared/package"
 
 // Mock fetch globally
 const mockFetch = vi.fn()
@@ -976,4 +977,53 @@ describe("getRooModels", () => {
 		// Should use 3.0.0 version settings (highest that's <= current plugin version)
 		expect(model.feature).toBe("current")
 	})
+
+	it("should apply highest versionedSettings for nightly builds (package name)", async () => {
+		const mockResponse = {
+			object: "list",
+			data: [
+				{
+					id: "test/nightly-version-model",
+					object: "model",
+					created: 1234567890,
+					owned_by: "test",
+					name: "Nightly Model",
+					description: "Model with multiple versioned settings",
+					context_window: 128000,
+					max_tokens: 8192,
+					type: "language",
+					pricing: {
+						input: "0.0001",
+						output: "0.0002",
+					},
+					settings: {
+						feature: "plain",
+					},
+					versionedSettings: {
+						"3.36.3": { feature: "v3" },
+						"2.0.0": { feature: "v2" },
+					},
+				},
+			],
+		}
+
+		mockFetch.mockResolvedValueOnce({
+			ok: true,
+			json: async () => mockResponse,
+		})
+
+		// Simulate nightly build via package name
+		const originalName = Package.name
+		;(Package as { name: string }).name = "roo-code-nightly"
+
+		try {
+			const models = await getRooModels(baseUrl, apiKey)
+			const model = models["test/nightly-version-model"] as Record<string, unknown>
+
+			// Should pick the highest available versionedSettings even though 3.36.3 > 0.0.7465
+			expect(model.feature).toBe("v3")
+		} finally {
+			;(Package as { name: string }).name = originalName
+		}
+	})
 })
diff --git a/src/api/providers/fetchers/__tests__/versionedSettings.spec.ts b/src/api/providers/fetchers/__tests__/versionedSettings.spec.ts
index 029f92b3017..9422c012678 100644
--- a/src/api/providers/fetchers/__tests__/versionedSettings.spec.ts
+++ b/src/api/providers/fetchers/__tests__/versionedSettings.spec.ts
@@ -5,6 +5,7 @@ import {
 	resolveVersionedSettings,
 	type VersionedSettings,
 } from "../versionedSettings"
+import { Package } from "../../../../shared/package"
 
 describe("versionedSettings", () => {
 	describe("compareSemver", () => {
@@ -113,6 +114,23 @@ describe("versionedSettings", () => {
 			const result = findHighestMatchingVersion(versionedSettings, "3.36.4")
 			expect(result).toBeUndefined()
 		})
+
+		it("should treat nightly builds (by package name) as always eligible and pick highest version", () => {
+			const versionedSettings: VersionedSettings = {
+				"3.36.3": { feature: "v3" },
+				"2.0.0": { feature: "v2" },
+			}
+
+			const originalName = Package.name
+			;(Package as { name: string }).name = "roo-code-nightly"
+
+			try {
+				const result = findHighestMatchingVersion(versionedSettings, "1.0.0")
+				expect(result).toBe("3.36.3")
+			} finally {
+				;(Package as { name: string }).name = originalName
+			}
+		})
 	})
 
 	describe("resolveVersionedSettings", () => {
diff --git a/src/api/providers/fetchers/versionedSettings.ts b/src/api/providers/fetchers/versionedSettings.ts
index 50ec0b89732..d644c683d35 100644
--- a/src/api/providers/fetchers/versionedSettings.ts
+++ b/src/api/providers/fetchers/versionedSettings.ts
@@ -2,6 +2,10 @@ import cmp from "semver-compare"
 
 import { Package } from "../../../shared/package"
 
+function isNightlyBuild(): boolean {
+	return Package.name.toLowerCase().includes("nightly")
+}
+
 /**
  * Type for versioned settings where the version is the key.
  * Each version key maps to a settings object that should be used
@@ -68,6 +72,16 @@ export function findHighestMatchingVersion(
 ): string | undefined {
 	const versions = Object.keys(versionedSettings)
 
+	if (versions.length === 0) {
+		return undefined
+	}
+
+	// Nightly builds should always pick the highest available versioned settings
+	if (isNightlyBuild()) {
+		versions.sort((a, b) => compareSemver(b, a))
+		return versions[0]
+	}
+
 	// Filter to versions that are <= currentVersion
 	const matchingVersions = versions.filter((version) => meetsMinimumVersion(version, currentVersion))