diff --git a/CHANGELOG.md b/CHANGELOG.md
index 22455198..41ed103a 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -2,6 +2,10 @@
 
 ## Unreleased
 
+### Changed
+
+- Always enable verbose (`-v`) flag when a log directory is configured (`coder.proxyLogDir`).
+
 ## [1.10.1](https://github.com/coder/vscode-coder/releases/tag/v1.10.1) 2025-08-13
 
 ### Fixed
diff --git a/src/commands.ts b/src/commands.ts
index b40ea56e..11ecf8b7 100644
--- a/src/commands.ts
+++ b/src/commands.ts
@@ -321,10 +321,19 @@ export class Commands {
 	 */
 	public async viewLogs(): Promise<void> {
 		if (!this.workspaceLogPath) {
-			vscode.window.showInformationMessage(
-				"No logs available. Make sure to set coder.proxyLogDirectory to get logs.",
-				this.workspaceLogPath || "<unset>",
-			);
+			vscode.window
+				.showInformationMessage(
+					"No logs available. Make sure to set coder.proxyLogDirectory to get logs.",
+					"Open Settings",
+				)
+				.then((action) => {
+					if (action === "Open Settings") {
+						vscode.commands.executeCommand(
+							"workbench.action.openSettings",
+							"coder.proxyLogDirectory",
+						);
+					}
+				});
 			return;
 		}
 		const uri = vscode.Uri.file(this.workspaceLogPath);
diff --git a/src/remote.ts b/src/remote.ts
index 40dd9072..9dbb1503 100644
--- a/src/remote.ts
+++ b/src/remote.ts
@@ -676,7 +676,7 @@ export class Remote {
 			"SSH proxy diagnostics are being written to",
 			logDir,
 		);
-		return ` --log-dir ${escapeCommandArg(logDir)}`;
+		return ` --log-dir ${escapeCommandArg(logDir)} -v`;
 	}
 
 	// updateSSHConfig updates the SSH configuration with a wildcard that handles