Session log: Windows setup continuation, bypass permissions fix, machine registration

Co-Authored-By: Claude Opus 4.6 (1M context) <noreply@anthropic.com>

.claude/memory/MEMORY.md

@@ -12,6 +12,7 @@
 
 ## Feedback
 - [D2TESTNAS SSH Access](feedback_d2testnas_ssh.md) - Use root@192.168.0.9 with Paper123!@#, not sysadmin
+- [Bypass Permissions Setting](feedback_bypass_permissions_setting.md) - Set permissions.defaultMode to bypassPermissions in settings.json on all machines
 
 ## Machine
 - [Windows Guru Setup Status](machine_windows_guru_setup_status.md) - Missing: Node.js, Ollama, GrepAI, .mcp.json. Has: Python, Git, SSH, credentials.md

.claude/memory/feedback_bypass_permissions_setting.md

@@ -0,0 +1,20 @@
+---
+name: Bypass Permissions Persistent Setting
+description: Configure settings.json on all machines to persist bypass permissions mode across context compressions
+type: feedback
+---
+
+Always set `permissions.defaultMode` to `"bypassPermissions"` in `~/.claude/settings.json` on all workstations.
+
+**Why:** The `--dangerously-skip-permissions` CLI flag is not preserved when Claude Code compresses context or resumes sessions -- the new process starts without the flag, causing unexpected permission prompts mid-session. This is a known bug (GitHub issue #21974).
+
+**How to apply:** On any new machine setup, ensure `~/.claude/settings.json` includes:
+```json
+{
+  "permissions": {
+    "defaultMode": "bypassPermissions"
+  },
+  "skipDangerousModePermissionPrompt": true
+}
+```
+This makes bypass mode the default without needing the CLI flag. Both keys are needed -- `defaultMode` sets the mode, `skipDangerousModePermissionPrompt` suppresses the warning dialog.