diff --git a/src/api/providers/openai.ts b/src/api/providers/openai.ts
index f5e4e4c985..dd166600d6 100644
--- a/src/api/providers/openai.ts
+++ b/src/api/providers/openai.ts
@@ -13,6 +13,7 @@ import {
 import type { ApiHandlerOptions } from "../../shared/api"
 
 import { XmlMatcher } from "../../utils/xml-matcher"
+import { extractApiVersionFromUrl } from "../../utils/azure-url-parser"
 
 import { convertToOpenAiMessages } from "../transform/openai-format"
 import { convertToR1Format } from "../transform/r1-format"
@@ -35,12 +36,24 @@ export class OpenAiHandler extends BaseProvider implements SingleCompletionHandl
 		super()
 		this.options = options
 
-		const baseURL = this.options.openAiBaseUrl ?? "https://api.openai.com/v1"
+		const originalBaseURL = this.options.openAiBaseUrl ?? "https://api.openai.com/v1"
 		const apiKey = this.options.openAiApiKey ?? "not-provided"
 		const isAzureAiInference = this._isAzureAiInference(this.options.openAiBaseUrl)
 		const urlHost = this._getUrlHost(this.options.openAiBaseUrl)
 		const isAzureOpenAi = urlHost === "azure.com" || urlHost.endsWith(".azure.com") || options.openAiUseAzure
 
+		// Extract API version from URL if present and no explicit azureApiVersion is set
+		let effectiveApiVersion = this.options.azureApiVersion
+		let baseURL = originalBaseURL
+
+		// Extract version for both Azure OpenAI and Azure AI Inference
+		if ((isAzureOpenAi || isAzureAiInference) && !effectiveApiVersion) {
+			const extractedVersion = extractApiVersionFromUrl(originalBaseURL)
+			if (extractedVersion) {
+				effectiveApiVersion = extractedVersion
+			}
+		}
+
 		const headers = {
 			...DEFAULT_HEADERS,
 			...(this.options.openAiHeaders || {}),
@@ -49,23 +62,23 @@ export class OpenAiHandler extends BaseProvider implements SingleCompletionHandl
 		if (isAzureAiInference) {
 			// Azure AI Inference Service (e.g., for DeepSeek) uses a different path structure
 			this.client = new OpenAI({
-				baseURL,
+				baseURL: originalBaseURL, // Keep original URL for AI Inference
 				apiKey,
 				defaultHeaders: headers,
-				defaultQuery: { "api-version": this.options.azureApiVersion || "2024-05-01-preview" },
+				defaultQuery: { "api-version": effectiveApiVersion || "2024-05-01-preview" },
 			})
 		} else if (isAzureOpenAi) {
 			// Azure API shape slightly differs from the core API shape:
 			// https://github.com/openai/openai-node?tab=readme-ov-file#microsoft-azure-openai
 			this.client = new AzureOpenAI({
-				baseURL,
+				baseURL: originalBaseURL, // Use original URL to maintain exact same behavior
 				apiKey,
-				apiVersion: this.options.azureApiVersion || azureOpenAiDefaultApiVersion,
+				apiVersion: effectiveApiVersion || azureOpenAiDefaultApiVersion,
 				defaultHeaders: headers,
 			})
 		} else {
 			this.client = new OpenAI({
-				baseURL,
+				baseURL: originalBaseURL,
 				apiKey,
 				defaultHeaders: headers,
 			})
diff --git a/src/utils/__tests__/azure-url-parser.test.ts b/src/utils/__tests__/azure-url-parser.test.ts
new file mode 100644
index 0000000000..44151c53b3
--- /dev/null
+++ b/src/utils/__tests__/azure-url-parser.test.ts
@@ -0,0 +1,190 @@
+import { describe, it, expect } from "vitest"
+import {
+	extractApiVersionFromUrl,
+	isAzureOpenAiUrl,
+	removeApiVersionFromUrl,
+	isValidAzureApiVersion,
+} from "../azure-url-parser"
+
+describe("azure-url-parser", () => {
+	describe("isValidAzureApiVersion", () => {
+		it("should return true for valid API version format YYYY-MM-DD", () => {
+			expect(isValidAzureApiVersion("2024-05-01")).toBe(true)
+			expect(isValidAzureApiVersion("2023-12-31")).toBe(true)
+		})
+
+		it("should return true for valid API version format YYYY-MM-DD-preview", () => {
+			expect(isValidAzureApiVersion("2024-05-01-preview")).toBe(true)
+			expect(isValidAzureApiVersion("2024-12-01-preview")).toBe(true)
+		})
+
+		it("should return false for invalid API version formats", () => {
+			expect(isValidAzureApiVersion("2024-5-1")).toBe(false) // Missing leading zeros
+			expect(isValidAzureApiVersion("24-05-01")).toBe(false) // Two-digit year
+			expect(isValidAzureApiVersion("2024/05/01")).toBe(false) // Wrong separator
+			expect(isValidAzureApiVersion("2024-05-01-alpha")).toBe(false) // Wrong suffix
+			expect(isValidAzureApiVersion("invalid-version")).toBe(false)
+			expect(isValidAzureApiVersion("")).toBe(false)
+		})
+	})
+
+	describe("extractApiVersionFromUrl", () => {
+		it("should extract API version from Azure OpenAI URL", () => {
+			const url =
+				"https://myresource.openai.azure.com/openai/deployments/mymodel/chat/completions?api-version=2024-05-01-preview"
+			const result = extractApiVersionFromUrl(url)
+			expect(result).toBe("2024-05-01-preview")
+		})
+
+		it("should extract API version from URL with multiple query parameters", () => {
+			const url =
+				"https://myresource.openai.azure.com/openai/deployments/mymodel/chat/completions?foo=bar&api-version=2024-12-01-preview&baz=qux"
+			const result = extractApiVersionFromUrl(url)
+			expect(result).toBe("2024-12-01-preview")
+		})
+
+		it("should return null when no api-version parameter exists", () => {
+			const url = "https://api.openai.com/v1/chat/completions"
+			const result = extractApiVersionFromUrl(url)
+			expect(result).toBeNull()
+		})
+
+		it("should return null for invalid URLs", () => {
+			const invalidUrl = "not-a-valid-url"
+			const result = extractApiVersionFromUrl(invalidUrl)
+			expect(result).toBeNull()
+		})
+
+		it("should handle empty api-version parameter", () => {
+			const url = "https://myresource.openai.azure.com/openai/deployments/mymodel/chat/completions?api-version="
+			const result = extractApiVersionFromUrl(url)
+			expect(result).toBe("")
+		})
+
+		it("should handle URL without query parameters", () => {
+			const url = "https://myresource.openai.azure.com/openai/deployments/mymodel/chat/completions"
+			const result = extractApiVersionFromUrl(url)
+			expect(result).toBeNull()
+		})
+
+		it("should handle URL with duplicate api-version parameters", () => {
+			const url =
+				"https://myresource.openai.azure.com/openai/deployments/mymodel/chat/completions?api-version=2024-05-01&api-version=2024-12-01"
+			const result = extractApiVersionFromUrl(url)
+			// URL.searchParams.get returns the first value
+			expect(result).toBe("2024-05-01")
+		})
+
+		it("should handle URL with malformed api-version parameter", () => {
+			const url =
+				"https://myresource.openai.azure.com/openai/deployments/mymodel/chat/completions?api-version=invalid-format"
+			const result = extractApiVersionFromUrl(url)
+			expect(result).toBe("invalid-format") // Still extracts it, validation is separate
+		})
+	})
+
+	describe("isAzureOpenAiUrl", () => {
+		it("should return true for Azure OpenAI URLs with .openai.azure.com", () => {
+			const url = "https://myresource.openai.azure.com/openai/deployments/mymodel/chat/completions"
+			const result = isAzureOpenAiUrl(url)
+			expect(result).toBe(true)
+		})
+
+		it("should return true for Azure URLs ending with .azure.com", () => {
+			const url = "https://myservice.azure.com/api/v1"
+			const result = isAzureOpenAiUrl(url)
+			expect(result).toBe(true)
+		})
+
+		it("should return true for URLs with /openai/deployments/ path", () => {
+			const url = "https://custom-domain.com/openai/deployments/mymodel/chat/completions"
+			const result = isAzureOpenAiUrl(url)
+			expect(result).toBe(true)
+		})
+
+		it("should return false for regular OpenAI URLs", () => {
+			const url = "https://api.openai.com/v1/chat/completions"
+			const result = isAzureOpenAiUrl(url)
+			expect(result).toBe(false)
+		})
+
+		it("should return false for other API URLs", () => {
+			const url = "https://api.anthropic.com/v1/messages"
+			const result = isAzureOpenAiUrl(url)
+			expect(result).toBe(false)
+		})
+
+		it("should return false for invalid URLs", () => {
+			const invalidUrl = "not-a-valid-url"
+			const result = isAzureOpenAiUrl(invalidUrl)
+			expect(result).toBe(false)
+		})
+
+		it("should handle case insensitive hostname matching", () => {
+			const url = "https://MYRESOURCE.OPENAI.AZURE.COM/openai/deployments/mymodel"
+			const result = isAzureOpenAiUrl(url)
+			expect(result).toBe(true)
+		})
+
+		it("should return false for malicious URLs trying to include Azure domain", () => {
+			const maliciousUrl = "https://evil.openai.azure.com.attacker.com/api/v1"
+			const result = isAzureOpenAiUrl(maliciousUrl)
+			expect(result).toBe(false)
+		})
+
+		it("should return true for root openai.azure.com domain", () => {
+			const url = "https://openai.azure.com/api/v1"
+			const result = isAzureOpenAiUrl(url)
+			expect(result).toBe(true)
+		})
+
+		it("should return false for Azure AI Inference Service URLs", () => {
+			const url = "https://myservice.services.ai.azure.com/models/deployments"
+			const result = isAzureOpenAiUrl(url)
+			expect(result).toBe(false)
+		})
+	})
+
+	describe("removeApiVersionFromUrl", () => {
+		it("should remove api-version parameter from URL", () => {
+			const url =
+				"https://myresource.openai.azure.com/openai/deployments/mymodel/chat/completions?api-version=2024-05-01-preview"
+			const result = removeApiVersionFromUrl(url)
+			expect(result).toBe("https://myresource.openai.azure.com/openai/deployments/mymodel/chat/completions")
+		})
+
+		it("should remove api-version parameter while preserving other parameters", () => {
+			const url =
+				"https://myresource.openai.azure.com/openai/deployments/mymodel/chat/completions?foo=bar&api-version=2024-05-01-preview&baz=qux"
+			const result = removeApiVersionFromUrl(url)
+			expect(result).toBe(
+				"https://myresource.openai.azure.com/openai/deployments/mymodel/chat/completions?foo=bar&baz=qux",
+			)
+		})
+
+		it("should return original URL when no api-version parameter exists", () => {
+			const url = "https://api.openai.com/v1/chat/completions?foo=bar"
+			const result = removeApiVersionFromUrl(url)
+			expect(result).toBe(url)
+		})
+
+		it("should return original URL for invalid URLs", () => {
+			const invalidUrl = "not-a-valid-url"
+			const result = removeApiVersionFromUrl(invalidUrl)
+			expect(result).toBe(invalidUrl)
+		})
+
+		it("should handle URL with only api-version parameter", () => {
+			const url =
+				"https://myresource.openai.azure.com/openai/deployments/mymodel/chat/completions?api-version=2024-05-01-preview"
+			const result = removeApiVersionFromUrl(url)
+			expect(result).toBe("https://myresource.openai.azure.com/openai/deployments/mymodel/chat/completions")
+		})
+
+		it("should handle URL without query parameters", () => {
+			const url = "https://myresource.openai.azure.com/openai/deployments/mymodel/chat/completions"
+			const result = removeApiVersionFromUrl(url)
+			expect(result).toBe(url)
+		})
+	})
+})
diff --git a/src/utils/azure-url-parser.ts b/src/utils/azure-url-parser.ts
new file mode 100644
index 0000000000..674e11dd14
--- /dev/null
+++ b/src/utils/azure-url-parser.ts
@@ -0,0 +1,82 @@
+/**
+ * Utility functions for parsing Azure OpenAI URLs and extracting API versions
+ */
+
+/**
+ * Validates if a string is a valid Azure API version format
+ * @param version The version string to validate
+ * @returns True if the version follows Azure API version format (YYYY-MM-DD or YYYY-MM-DD-preview)
+ */
+export function isValidAzureApiVersion(version: string): boolean {
+	if (!version) return false
+
+	// Azure API versions follow the pattern: YYYY-MM-DD or YYYY-MM-DD-preview
+	const versionPattern = /^\d{4}-\d{2}-\d{2}(-preview)?$/
+	return versionPattern.test(version)
+}
+
+/**
+ * Extracts the API version from an Azure OpenAI URL query parameter
+ * @param url The Azure OpenAI URL that may contain an api-version query parameter
+ * @returns The extracted API version string, or null if not found
+ */
+export function extractApiVersionFromUrl(url: string): string | null {
+	try {
+		const urlObj = new URL(url)
+		const apiVersion = urlObj.searchParams.get("api-version")
+
+		// Validate the extracted version format
+		if (apiVersion && !isValidAzureApiVersion(apiVersion)) {
+			console.warn(`Invalid Azure API version format: ${apiVersion}`)
+		}
+
+		return apiVersion
+	} catch (error) {
+		// Invalid URL format
+		return null
+	}
+}
+
+/**
+ * Checks if a URL appears to be an Azure OpenAI URL
+ * @param url The URL to check
+ * @returns True if the URL appears to be an Azure OpenAI URL
+ */
+export function isAzureOpenAiUrl(url: string): boolean {
+	try {
+		const urlObj = new URL(url)
+		const host = urlObj.host.toLowerCase()
+
+		// Exclude Azure AI Inference Service URLs
+		if (host.endsWith(".services.ai.azure.com")) {
+			return false
+		}
+
+		// Check for Azure OpenAI hostname patterns
+		// Use endsWith to prevent matching malicious URLs like evil.openai.azure.com.attacker.com
+		return (
+			host.endsWith(".openai.azure.com") ||
+			host === "openai.azure.com" ||
+			host.endsWith(".azure.com") ||
+			urlObj.pathname.includes("/openai/deployments/")
+		)
+	} catch (error) {
+		return false
+	}
+}
+
+/**
+ * Removes the api-version query parameter from a URL
+ * @param url The URL to clean
+ * @returns The URL without the api-version parameter
+ */
+export function removeApiVersionFromUrl(url: string): string {
+	try {
+		const urlObj = new URL(url)
+		urlObj.searchParams.delete("api-version")
+		return urlObj.toString()
+	} catch (error) {
+		// Return original URL if parsing fails
+		return url
+	}
+}
diff --git a/webview-ui/src/components/settings/providers/OpenAICompatible.tsx b/webview-ui/src/components/settings/providers/OpenAICompatible.tsx
index 736b0253c4..654ed73220 100644
--- a/webview-ui/src/components/settings/providers/OpenAICompatible.tsx
+++ b/webview-ui/src/components/settings/providers/OpenAICompatible.tsx
@@ -12,6 +12,12 @@ import {
 	openAiModelInfoSaneDefaults,
 } from "@roo-code/types"
 
+import {
+	extractApiVersionFromUrl,
+	isAzureOpenAiUrl,
+	isValidAzureApiVersion,
+} from "../../../../../src/utils/azure-url-parser"
+
 import { ExtensionMessage } from "@roo/ExtensionMessage"
 
 import { useAppTranslation } from "@src/i18n/TranslationContext"
@@ -41,6 +47,12 @@ export const OpenAICompatible = ({
 	const [azureApiVersionSelected, setAzureApiVersionSelected] = useState(!!apiConfiguration?.azureApiVersion)
 	const [openAiLegacyFormatSelected, setOpenAiLegacyFormatSelected] = useState(!!apiConfiguration?.openAiLegacyFormat)
 
+	// Check if API version can be extracted from the base URL
+	const baseUrl = apiConfiguration?.openAiBaseUrl || ""
+	const extractedApiVersion = extractApiVersionFromUrl(baseUrl)
+	const isAzureUrl = isAzureOpenAiUrl(baseUrl)
+	const showApiVersionExtraction = isAzureUrl && extractedApiVersion && !azureApiVersionSelected
+
 	const [openAiModels, setOpenAiModels] = useState<Record<string, ModelInfo> | null>(null)
 
 	const [customHeaders, setCustomHeaders] = useState<[string, string][]>(() => {
@@ -194,12 +206,31 @@ export const OpenAICompatible = ({
 					}}>
 					{t("settings:modelInfo.azureApiVersion")}
 				</Checkbox>
+				{showApiVersionExtraction && (
+					<div
+						className="text-sm text-vscode-descriptionForeground ml-6 mb-2"
+						dangerouslySetInnerHTML={{
+							__html: t("settings:modelInfo.azureApiVersionDetected", { version: extractedApiVersion }),
+						}}
+					/>
+				)}
 				{azureApiVersionSelected && (
 					<VSCodeTextField
 						value={apiConfiguration?.azureApiVersion || ""}
 						onInput={handleInputChange("azureApiVersion")}
 						placeholder={`Default: ${azureOpenAiDefaultApiVersion}`}
 						className="w-full mt-1"
+						style={{
+							borderColor: (() => {
+								const value = apiConfiguration?.azureApiVersion
+								if (!value) {
+									return "var(--vscode-input-border)"
+								}
+								return isValidAzureApiVersion(value)
+									? "var(--vscode-charts-green)"
+									: "var(--vscode-errorForeground)"
+							})(),
+						}}
 					/>
 				)}
 			</div>
diff --git a/webview-ui/src/i18n/locales/ca/settings.json b/webview-ui/src/i18n/locales/ca/settings.json
index 15018e64ab..d01915fa63 100644
--- a/webview-ui/src/i18n/locales/ca/settings.json
+++ b/webview-ui/src/i18n/locales/ca/settings.json
@@ -631,6 +631,7 @@
 		"enableR1FormatTips": "S'ha d'activat quan s'utilitzen models R1 com el QWQ per evitar errors 400",
 		"useAzure": "Utilitzar Azure",
 		"azureApiVersion": "Establir versió de l'API d'Azure",
+		"azureApiVersionDetected": "Versió de l'API detectada a l'URL base: <strong>{{version}}</strong><br />Aquesta s'utilitzarà automàticament. Activa la casella de selecció anterior per sobreescriure-la.",
 		"gemini": {
 			"freeRequests": "* Gratuït fins a {{count}} sol·licituds per minut. Després d'això, la facturació depèn de la mida del prompt.",
 			"pricingDetails": "Per a més informació, consulteu els detalls de preus.",
diff --git a/webview-ui/src/i18n/locales/de/settings.json b/webview-ui/src/i18n/locales/de/settings.json
index bb5ed1146b..8c7ef5c0bb 100644
--- a/webview-ui/src/i18n/locales/de/settings.json
+++ b/webview-ui/src/i18n/locales/de/settings.json
@@ -631,6 +631,7 @@
 		"enableR1FormatTips": "Muss bei Verwendung von R1-Modellen wie QWQ aktiviert werden, um 400er-Fehler zu vermeiden",
 		"useAzure": "Azure verwenden",
 		"azureApiVersion": "Azure API-Version festlegen",
+		"azureApiVersionDetected": "In der Basis-URL erkannte API-Version: <strong>{{version}}</strong><br />Diese wird automatisch verwendet. Aktiviere das obige Kontrollkästchen, um dies zu überschreiben.",
 		"gemini": {
 			"freeRequests": "* Kostenlos bis zu {{count}} Anfragen pro Minute. Danach hängt die Abrechnung von der Prompt-Größe ab.",
 			"pricingDetails": "Weitere Informationen finden Sie unter Preisdetails.",
diff --git a/webview-ui/src/i18n/locales/en/settings.json b/webview-ui/src/i18n/locales/en/settings.json
index 728e856502..706a8e86b8 100644
--- a/webview-ui/src/i18n/locales/en/settings.json
+++ b/webview-ui/src/i18n/locales/en/settings.json
@@ -631,6 +631,7 @@
 		"enableR1FormatTips": "Must be enabled when using R1 models such as QWQ to prevent 400 errors",
 		"useAzure": "Use Azure",
 		"azureApiVersion": "Set Azure API version",
+		"azureApiVersionDetected": "API version detected in Base URL: <strong>{{version}}</strong><br />This will be used automatically. Enable the checkbox above to override.",
 		"gemini": {
 			"freeRequests": "* Free up to {{count}} requests per minute. After that, billing depends on prompt size.",
 			"pricingDetails": "For more info, see pricing details.",
diff --git a/webview-ui/src/i18n/locales/es/settings.json b/webview-ui/src/i18n/locales/es/settings.json
index 5836933b46..c502e677e5 100644
--- a/webview-ui/src/i18n/locales/es/settings.json
+++ b/webview-ui/src/i18n/locales/es/settings.json
@@ -631,6 +631,7 @@
 		"enableR1FormatTips": "Debe habilitarse al utilizar modelos R1 como QWQ, para evitar el error 400",
 		"useAzure": "Usar Azure",
 		"azureApiVersion": "Establecer versión de API de Azure",
+		"azureApiVersionDetected": "Versión de la API detectada en la URL base: <strong>{{version}}</strong><br />Se utilizará automáticamente. Habilita la casilla de verificación anterior para anularla.",
 		"gemini": {
 			"freeRequests": "* Gratis hasta {{count}} solicitudes por minuto. Después de eso, la facturación depende del tamaño del prompt.",
 			"pricingDetails": "Para más información, consulte los detalles de precios.",
diff --git a/webview-ui/src/i18n/locales/fr/settings.json b/webview-ui/src/i18n/locales/fr/settings.json
index 833a789e5a..6aa2302404 100644
--- a/webview-ui/src/i18n/locales/fr/settings.json
+++ b/webview-ui/src/i18n/locales/fr/settings.json
@@ -631,6 +631,7 @@
 		"enableR1FormatTips": "Doit être activé lors de l'utilisation de modèles R1 tels que QWQ, pour éviter l'erreur 400",
 		"useAzure": "Utiliser Azure",
 		"azureApiVersion": "Définir la version de l'API Azure",
+		"azureApiVersionDetected": "Version de l'API détectée dans l'URL de base : <strong>{{version}}</strong><br />Celle-ci sera utilisée automatiquement. Cochez la case ci-dessus pour la remplacer.",
 		"gemini": {
 			"freeRequests": "* Gratuit jusqu'à {{count}} requêtes par minute. Après cela, la facturation dépend de la taille du prompt.",
 			"pricingDetails": "Pour plus d'informations, voir les détails de tarification.",
diff --git a/webview-ui/src/i18n/locales/hi/settings.json b/webview-ui/src/i18n/locales/hi/settings.json
index 0749943508..127a3a633d 100644
--- a/webview-ui/src/i18n/locales/hi/settings.json
+++ b/webview-ui/src/i18n/locales/hi/settings.json
@@ -631,6 +631,7 @@
 		"enableR1FormatTips": "QWQ जैसी R1 मॉडलों का उपयोग करते समय इसे सक्षम करना आवश्यक है, ताकि 400 त्रुटि से बचा जा सके",
 		"useAzure": "Azure का उपयोग करें",
 		"azureApiVersion": "Azure API संस्करण सेट करें",
+		"azureApiVersionDetected": "बेस यूआरएल में एपीआई संस्करण का पता चला: <strong>{{version}}</strong><br />यह स्वचालित रूप से उपयोग किया जाएगा। ओवरराइड करने के लिए ऊपर दिए गए चेकबॉक्स को सक्षम करें।",
 		"gemini": {
 			"freeRequests": "* प्रति मिनट {{count}} अनुरोधों तक मुफ्त। उसके बाद, बिलिंग प्रॉम्प्ट आकार पर निर्भर करती है।",
 			"pricingDetails": "अधिक जानकारी के लिए, मूल्य निर्धारण विवरण देखें।",
diff --git a/webview-ui/src/i18n/locales/id/settings.json b/webview-ui/src/i18n/locales/id/settings.json
index 4a0c51d39d..b809252761 100644
--- a/webview-ui/src/i18n/locales/id/settings.json
+++ b/webview-ui/src/i18n/locales/id/settings.json
@@ -660,6 +660,7 @@
 		"enableR1FormatTips": "Harus diaktifkan saat menggunakan model R1 seperti QWQ untuk mencegah error 400",
 		"useAzure": "Gunakan Azure",
 		"azureApiVersion": "Atur versi API Azure",
+		"azureApiVersionDetected": "Versi API terdeteksi di URL Dasar: <strong>{{version}}</strong><br />Ini akan digunakan secara otomatis. Aktifkan kotak centang di atas untuk menimpa.",
 		"gemini": {
 			"freeRequests": "* Gratis hingga {{count}} permintaan per menit. Setelah itu, penagihan tergantung pada ukuran prompt.",
 			"pricingDetails": "Untuk info lebih lanjut, lihat detail harga.",
diff --git a/webview-ui/src/i18n/locales/it/settings.json b/webview-ui/src/i18n/locales/it/settings.json
index 9d9be82868..1b463d017c 100644
--- a/webview-ui/src/i18n/locales/it/settings.json
+++ b/webview-ui/src/i18n/locales/it/settings.json
@@ -631,6 +631,7 @@
 		"enableR1FormatTips": "Deve essere abilitato quando si utilizzano modelli R1 come QWQ, per evitare l'errore 400",
 		"useAzure": "Usa Azure",
 		"azureApiVersion": "Imposta versione API Azure",
+		"azureApiVersionDetected": "Versione API rilevata nell'URL di base: <strong>{{version}}</strong><br />Verrà utilizzata automaticamente. Abilita la casella di controllo sopra per sovrascriverla.",
 		"gemini": {
 			"freeRequests": "* Gratuito fino a {{count}} richieste al minuto. Dopo, la fatturazione dipende dalla dimensione del prompt.",
 			"pricingDetails": "Per maggiori informazioni, vedi i dettagli sui prezzi.",
diff --git a/webview-ui/src/i18n/locales/ja/settings.json b/webview-ui/src/i18n/locales/ja/settings.json
index 9fc03cbfb1..ee778d27b1 100644
--- a/webview-ui/src/i18n/locales/ja/settings.json
+++ b/webview-ui/src/i18n/locales/ja/settings.json
@@ -631,6 +631,7 @@
 		"enableR1FormatTips": "QWQなどのR1モデルを使用する際には、有効にする必要があります。400エラーを防ぐために",
 		"useAzure": "Azureを使用",
 		"azureApiVersion": "Azure APIバージョンを設定",
+		"azureApiVersionDetected": "ベースURLでAPIバージョンが検出されました: <strong>{{version}}</strong><br />これは自動的に使用されます。上書きするには、上のチェックボックスを有効にしてください。",
 		"gemini": {
 			"freeRequests": "* 1分間あたり{{count}}リクエストまで無料。それ以降は、プロンプトサイズに応じて課金されます。",
 			"pricingDetails": "詳細は価格情報をご覧ください。",
diff --git a/webview-ui/src/i18n/locales/ko/settings.json b/webview-ui/src/i18n/locales/ko/settings.json
index 219daa05a4..e6f1bd7246 100644
--- a/webview-ui/src/i18n/locales/ko/settings.json
+++ b/webview-ui/src/i18n/locales/ko/settings.json
@@ -631,6 +631,7 @@
 		"enableR1FormatTips": "QWQ와 같은 R1 모델을 사용할 때 활성화해야 하며, 400 오류를 방지합니다",
 		"useAzure": "Azure 사용",
 		"azureApiVersion": "Azure API 버전 설정",
+		"azureApiVersionDetected": "기본 URL에서 API 버전 감지됨: <strong>{{version}}</strong><br />자동으로 사용됩니다. 재정의하려면 위의 확인란을 활성화하세요.",
 		"gemini": {
 			"freeRequests": "* 분당 {{count}}개의 요청까지 무료. 이후에는 프롬프트 크기에 따라 요금이 부과됩니다.",
 			"pricingDetails": "자세한 내용은 가격 정보를 참조하세요.",
diff --git a/webview-ui/src/i18n/locales/nl/settings.json b/webview-ui/src/i18n/locales/nl/settings.json
index e184f4d85e..ec9515ca32 100644
--- a/webview-ui/src/i18n/locales/nl/settings.json
+++ b/webview-ui/src/i18n/locales/nl/settings.json
@@ -631,6 +631,7 @@
 		"enableR1FormatTips": "Moet ingeschakeld zijn bij gebruik van R1-modellen zoals QWQ om 400-fouten te voorkomen",
 		"useAzure": "Azure gebruiken",
 		"azureApiVersion": "Azure API-versie instellen",
+		"azureApiVersionDetected": "API-versie gedetecteerd in basis-URL: <strong>{{version}}</strong><br />Deze wordt automatisch gebruikt. Schakel het selectievakje hierboven in om te overschrijven.",
 		"gemini": {
 			"freeRequests": "* Gratis tot {{count}} verzoeken per minuut. Daarna is de prijs afhankelijk van de promptgrootte.",
 			"pricingDetails": "Zie prijsdetails voor meer info.",
diff --git a/webview-ui/src/i18n/locales/pl/settings.json b/webview-ui/src/i18n/locales/pl/settings.json
index 23d3ce707d..64f1a60f8e 100644
--- a/webview-ui/src/i18n/locales/pl/settings.json
+++ b/webview-ui/src/i18n/locales/pl/settings.json
@@ -631,6 +631,7 @@
 		"enableR1FormatTips": "Należy włączyć podczas korzystania z modeli R1, takich jak QWQ, aby uniknąć błędu 400",
 		"useAzure": "Użyj Azure",
 		"azureApiVersion": "Ustaw wersję API Azure",
+		"azureApiVersionDetected": "Wykryto wersję API w bazowym adresie URL: <strong>{{version}}</strong><br />Zostanie ona użyta automatycznie. Zaznacz powyższe pole wyboru, aby nadpisać.",
 		"gemini": {
 			"freeRequests": "* Darmowe do {{count}} zapytań na minutę. Po tym, rozliczanie zależy od rozmiaru podpowiedzi.",
 			"pricingDetails": "Więcej informacji znajdziesz w szczegółach cennika.",
diff --git a/webview-ui/src/i18n/locales/pt-BR/settings.json b/webview-ui/src/i18n/locales/pt-BR/settings.json
index 102036622c..7630b92e60 100644
--- a/webview-ui/src/i18n/locales/pt-BR/settings.json
+++ b/webview-ui/src/i18n/locales/pt-BR/settings.json
@@ -631,6 +631,7 @@
 		"enableR1FormatTips": "Deve ser ativado ao usar modelos R1 como QWQ, para evitar erro 400",
 		"useAzure": "Usar Azure",
 		"azureApiVersion": "Definir versão da API Azure",
+		"azureApiVersionDetected": "Versão da API detectada na URL base: <strong>{{version}}</strong><br />Isso será usado automaticamente. Habilite a caixa de seleção acima para substituir.",
 		"gemini": {
 			"freeRequests": "* Gratuito até {{count}} requisições por minuto. Depois disso, a cobrança depende do tamanho do prompt.",
 			"pricingDetails": "Para mais informações, consulte os detalhes de preços.",
diff --git a/webview-ui/src/i18n/locales/ru/settings.json b/webview-ui/src/i18n/locales/ru/settings.json
index 5952dd8c89..85d7c67e60 100644
--- a/webview-ui/src/i18n/locales/ru/settings.json
+++ b/webview-ui/src/i18n/locales/ru/settings.json
@@ -631,6 +631,7 @@
 		"enableR1FormatTips": "Необходимо включить при использовании моделей R1 (например, QWQ), чтобы избежать ошибок 400",
 		"useAzure": "Использовать Azure",
 		"azureApiVersion": "Установить версию API Azure",
+		"azureApiVersionDetected": "Версия API обнаружена в базовом URL: <strong>{{version}}</strong><br />Она будет использоваться автоматически. Включите флажок выше, чтобы переопределить.",
 		"gemini": {
 			"freeRequests": "* Бесплатно до {{count}} запросов в минуту. Далее тарификация зависит от размера подсказки.",
 			"pricingDetails": "Подробнее о ценах.",
diff --git a/webview-ui/src/i18n/locales/tr/settings.json b/webview-ui/src/i18n/locales/tr/settings.json
index 625ca4d5ea..832958a7d7 100644
--- a/webview-ui/src/i18n/locales/tr/settings.json
+++ b/webview-ui/src/i18n/locales/tr/settings.json
@@ -631,6 +631,7 @@
 		"enableR1FormatTips": "QWQ gibi R1 modelleri kullanıldığında etkinleştirilmelidir, 400 hatası alınmaması için",
 		"useAzure": "Azure kullan",
 		"azureApiVersion": "Azure API sürümünü ayarla",
+		"azureApiVersionDetected": "Temel URL'de API sürümü algılandı: <strong>{{version}}</strong><br />Bu otomatik olarak kullanılacaktır. Geçersiz kılmak için yukarıdaki onay kutusunu etkinleştirin.",
 		"gemini": {
 			"freeRequests": "* Dakikada {{count}} isteğe kadar ücretsiz. Bundan sonra, ücretlendirme istem boyutuna bağlıdır.",
 			"pricingDetails": "Daha fazla bilgi için fiyatlandırma ayrıntılarına bakın.",
diff --git a/webview-ui/src/i18n/locales/vi/settings.json b/webview-ui/src/i18n/locales/vi/settings.json
index 52a9db5b93..500317fcc8 100644
--- a/webview-ui/src/i18n/locales/vi/settings.json
+++ b/webview-ui/src/i18n/locales/vi/settings.json
@@ -631,6 +631,7 @@
 		"enableR1FormatTips": "Cần kích hoạt khi sử dụng các mô hình R1 như QWQ, để tránh lỗi 400",
 		"useAzure": "Sử dụng Azure",
 		"azureApiVersion": "Đặt phiên bản API Azure",
+		"azureApiVersionDetected": "Phiên bản API được phát hiện trong URL cơ sở: <strong>{{version}}</strong><br />Phiên bản này sẽ được sử dụng tự động. Bật hộp kiểm ở trên để ghi đè.",
 		"gemini": {
 			"freeRequests": "* Miễn phí đến {{count}} yêu cầu mỗi phút. Sau đó, thanh toán phụ thuộc vào kích thước lời nhắc.",
 			"pricingDetails": "Để biết thêm thông tin, xem chi tiết giá.",
diff --git a/webview-ui/src/i18n/locales/zh-CN/settings.json b/webview-ui/src/i18n/locales/zh-CN/settings.json
index 151ee9e744..a7bc65d473 100644
--- a/webview-ui/src/i18n/locales/zh-CN/settings.json
+++ b/webview-ui/src/i18n/locales/zh-CN/settings.json
@@ -631,6 +631,7 @@
 		"enableR1FormatTips": "使用 QWQ 等 R1 系列模型时必须启用，避免出现 400 错误",
 		"useAzure": "使用 Azure 服务",
 		"azureApiVersion": "设置 Azure API 版本",
+		"azureApiVersionDetected": "在基本 URL 中检测到 API 版本：<strong>{{version}}</strong><br />将自动使用此版本。若要覆盖，请启用上方的复选框。",
 		"gemini": {
 			"freeRequests": "* 每分钟免费 {{count}} 个请求。之后，计费取决于提示大小。",
 			"pricingDetails": "有关更多信息，请参阅定价详情。",
diff --git a/webview-ui/src/i18n/locales/zh-TW/settings.json b/webview-ui/src/i18n/locales/zh-TW/settings.json
index ab4caeea5b..4f0bbbd5da 100644
--- a/webview-ui/src/i18n/locales/zh-TW/settings.json
+++ b/webview-ui/src/i18n/locales/zh-TW/settings.json
@@ -631,6 +631,7 @@
 		"enableR1FormatTips": "使用 QWQ 等 R1 模型時必須啟用，以避免發生 400 錯誤",
 		"useAzure": "使用 Azure",
 		"azureApiVersion": "設定 Azure API 版本",
+		"azureApiVersionDetected": "在基底 URL 中偵測到 API 版本：<strong>{{version}}</strong><br />將自動使用此版本。若要覆寫，請啟用上方的核取方塊。",
 		"gemini": {
 			"freeRequests": "* 每分鐘可免費使用 {{count}} 次請求，超過後將依提示大小計費。",
 			"pricingDetails": "詳細資訊請參閱定價說明。",