diff --git a/src/vs/code/electron-main/window.ts b/src/vs/code/electron-main/window.ts
index e8116b8899d..78095162798 100644
--- a/src/vs/code/electron-main/window.ts
+++ b/src/vs/code/electron-main/window.ts
@@ -601,9 +601,12 @@ export class CodeWindow extends Disposable implements ICodeWindow {
 		}
 		// Do not set to empty configuration at startup if setting is empty to not override configuration through CLI options:
 		const env = process.env;
-		const newHttpProxy = (this.configurationService.getValue<string>('http.proxy') || '').trim()
+		let newHttpProxy = (this.configurationService.getValue<string>('http.proxy') || '').trim()
 			|| (env.https_proxy || process.env.HTTPS_PROXY || process.env.http_proxy || process.env.HTTP_PROXY || '').trim() // Not standardized.
 			|| undefined;
+		if (newHttpProxy?.endsWith('/')) {
+			newHttpProxy = newHttpProxy.substr(0, newHttpProxy.length - 1);
+		}
 		const newNoProxy = (env.no_proxy || env.NO_PROXY || '').trim() || undefined; // Not standardized.
 		if ((newHttpProxy || '').indexOf('@') === -1 && (newHttpProxy !== this.currentHttpProxy || newNoProxy !== this.currentNoProxy)) {
 			this.currentHttpProxy = newHttpProxy;