diff --git a/Tasks.md b/Tasks.md
index 1122da5..529abbd 100644
--- a/Tasks.md
+++ b/Tasks.md
@@ -69,13 +69,6 @@ This document defines the complete project roadmap and task tracking system for
 
 | ID | Title | Status | Type |
 |---|---|---|---|
-| [NUT-001](#nut-001) | Establish Repository Structure | Fixed | Foundation |
-| [NUT-002](#nut-002) | Implement Shared Rust Backend Library | Fixed | Foundation |
-| [NUT-003](#nut-003) | Implement WebDAV Upload Logic | Fixed | Feature |
-| [NUT-004](#nut-004) | Implement OCS Share Link Generation | Fixed | Feature |
-| [NUT-005](#nut-005) | Implement Direct Download URL Builder | Fixed | Feature |
-| [NUT-006](#nut-006) | Implement Credential Storage System | Fixed | Feature |
-| [NUT-007](#nut-007) | Implement Multi-Account Support (Backend) | Fixed | Feature |
 | [NUT-008](#nut-008) | Implement CLI Frontend | Triage | Feature |
 | [NUT-009](#nut-009) | Implement CLI Output Formatting Options | Triage | Feature |
 | [NUT-010](#nut-010) | Implement CLI Multi-file Upload Support | Triage | Feature |
@@ -89,6 +82,14 @@ This document defines the complete project roadmap and task tracking system for
 | [NUT-018](#nut-018) | Implement Packaging for macOS, Windows, Linux | Triage | Chore |
 | [NUT-019](#nut-019) | Implement Homebrew/Winget/Chocolatey Manifests | Triage | Chore |
 | [NUT-020](#nut-020) | Write Documentation + Examples | Triage | Chore |
+| [NUT-021](#nut-021) | Support Headless & SSH Remote Authentication Modes | Triage | Feature |
+| [NUT-001](#nut-001) | Establish Repository Structure | Fixed | Foundation |
+| [NUT-002](#nut-002) | Implement Shared Rust Backend Library | Fixed | Foundation |
+| [NUT-003](#nut-003) | Implement WebDAV Upload Logic | Fixed | Feature |
+| [NUT-004](#nut-004) | Implement OCS Share Link Generation | Fixed | Feature |
+| [NUT-005](#nut-005) | Implement Direct Download URL Builder | Fixed | Feature |
+| [NUT-006](#nut-006) | Implement Credential Storage System | Fixed | Feature |
+| [NUT-007](#nut-007) | Implement Multi-Account Support (Backend) | Fixed | Feature |
 
 ---
 
@@ -490,6 +491,26 @@ Write documentation for installation, usage, examples, and API reference.
 - NUT-017  
 - NUT-018
 
+
+<a id="nut-021" class="task" data-status="triage" data-task-type="feature"></a>
+### Support Headless & SSH Remote Authentication Modes  
+**ID:** NUT-021  
+**Status:** Triage  
+**Type:** Feature  
+
+**Description:**  
+Ensure smooth authentication experiences when running the CLI over SSH or in headless environments where a local graphical browser cannot be launched automatically.
+
+**Requirements:**  
+- [ ] Terminal URL fallback: print clickable Login Flow v2 URL in terminal when browser fails to launch  
+- [ ] Add `--no-browser` flag to print URL and wait for authorization without attempting to open desktop browser  
+- [ ] Add interactive manual terminal prompt (`--manual`) for username and app password input  
+- [ ] Add non-interactive flag inputs (`--username`, `--app-password`) for automated provisioning and CI/CD  
+
+**Dependencies:**  
+- NUT-006  
+- NUT-008
+
 ---
 
 <a id="task-system-rules"></a>