Resolve Mac RDP Certificate Trust Issues and Authentication Loops

draft · remote-access rdpmac-rdpaccount-lockout

Generated by docuprocessor (prompt article/v3) · 2026-04-22 08:35

Source thread

thread_id: spaces/AAAA05BdS6s/threads/1aBgPVjPGNQ · 7 msgs · first 2024-07-08 · participants: Tech ATech BTech C

Tech A 2024-07-08 14:12

@all hey guys, can someone help me with the following, we got a request for a remote user, trying to access with Remote Desktop on a Mac, customer was trying to connect to the 172.17.130.10 server with the old domain hqrc, and a certificate error was showing, I tried adding a new Remote Session with the 172.17.130.11 PDS HEADQUARTERS - HQ-SVR2 TS, with the PDSMGMT\EAMR account, but I am still getting the same error message. Any suggestions? Thanks.

image/png image.png

**RDP Certificate Warning Dialog – macOS** A macOS Remote Desktop Protocol (RDP) connection dialog is displayed, warning that the certificate for host **172.17.130.11** cannot be verified to a root certificate. The certificate shown is **\*.pdsmgmt.local**, issued by **pdsmgmt-DC01-CA**, expiring **Wednesday, June 24, 2026 at 9:33:43 PM Eastern Daylight Time**. A red error indicator states **"\*.pdsmgmt.local certificate is not trusted"**, with options to Cancel or Continue.

Tech B 2024-07-08 14:14

click continue

Tech A 2024-07-08 14:16

Get a sign in loop, asking for password and never gets authenticated.

Tech B 2024-07-08 14:16

can u install it?

Tech A 2024-07-08 14:17

Do you mean install the certificate or uninstall and reinstall the app in the pc? btw, I tried to sign in with the user in another pc and it's not allowing me either, do you think that could be a password problem maybe?

Tech A 2024-07-08 14:45

It was the password.

Tech C 2024-07-08 15:11

Also

image/jpeg Image_20240708_101107_654.jpeg

The image displays a text-based instructional guide (steps 2–5) for importing and trusting a VPN certificate on macOS using Keychain Access. Key on-screen instructions reference navigating to **Applications > Utilities > Keychain Access**, using **File > Import Items**, setting the **Secure Sockets Layer (SSL)** trust setting to **"Always Trust"**, and entering VPN provider credentials. No error codes, equipment labels, indicator lights, or hardware components are visible.

---
title: "Resolve Mac RDP Certificate Trust Issues and Authentication Loops"
category: remote-access
tags: ["rdp", "mac-rdp", "account-lockout"]
source_thread_id: "spaces/AAAA05BdS6s/threads/1aBgPVjPGNQ"
source_space: "spaces/AAAA05BdS6s"
generated_at: "2026-04-22T08:35:32"
participants: ["Tech A", "Tech B", "Tech C"]
---

# Resolve Mac RDP Certificate Trust Issues and Authentication Loops

## Problem
Mac users connecting via Remote Desktop to Windows servers may encounter certificate trust warnings for domain certificates (e.g., `*.pdsmgmt.local` issued by internal CA). Even after clicking "Continue" to bypass the certificate warning, users may experience authentication loops where the system repeatedly prompts for credentials without successfully connecting. This can occur when connecting to servers like 172.17.130.11 using domain accounts.

## Resolution
1. **Address the authentication loop first**: Verify the user account password is correct by testing login on another machine or directly on the target server
2. **For the certificate trust issue**: Import and trust the certificate in macOS Keychain Access:
   - Navigate to **Applications > Utilities > Keychain Access**
   - Use **File > Import Items** to import the certificate
   - Set the **Secure Sockets Layer (SSL)** trust setting to **"Always Trust"**
3. **Alternative workaround**: Click "Continue" on the certificate warning dialog to proceed with the untrusted certificate, though this is less secure than properly importing it

The authentication loop was resolved by correcting the user password in this case.

## References
- Source discussion: `spaces/AAAA05BdS6s/threads/1aBgPVjPGNQ`
- Attachments:
  - ![image.png](../attachments/1aBgPVjPGNQ.1aBgPVjPGNQ/image.png) — **RDP Certificate Warning Dialog – macOS**
  - ![Image_20240708_101107_654.jpeg](../attachments/1aBgPVjPGNQ.ymD-cgyYFLY/Image_20240708_101107_654.jpeg) — The image displays a text-based instructional guide (steps 2–5) for importing and trusting a VPN certificate on macOS using Keychain Access. Key on-screen instructions reference navigating to **Applications > Utilities > Keychain Access**, using **File > Import Items**, setting the **Secure Sockets Layer (SSL)** trust setting to **"Always Trust"**, and entering VPN provider credentials. No error codes, equipment labels, indicator lights, or hardware components are visible.

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