diff --git a/.github/workflows/codecov-upload.yml b/.github/workflows/codecov-upload.yml
index d16b2192..8e6decec 100644
--- a/.github/workflows/codecov-upload.yml
+++ b/.github/workflows/codecov-upload.yml
@@ -35,7 +35,7 @@ jobs:
           exit ${PIPESTATUS[0]}
 
       - name: Upload backend coverage to Codecov
-        uses: codecov/codecov-action@5a1091511ad55cbe89839c7260b706298ca349f7 # v5
+        uses: codecov/codecov-action@671740ac38dd9b0130fbe1cec585b89eea48d3de # v5
         with:
           token: ${{ secrets.CODECOV_TOKEN }}
           files: ./backend/coverage.txt
@@ -54,7 +54,7 @@ jobs:
       - name: Set up Node.js
         uses: actions/setup-node@395ad3262231945c25e8478fd5baf05154b1d79f # v6
         with:
-          node-version: '24.11.1'
+          node-version: '24.12.0'
           cache: 'npm'
           cache-dependency-path: frontend/package-lock.json
 
@@ -69,7 +69,7 @@ jobs:
           exit ${PIPESTATUS[0]}
 
       - name: Upload frontend coverage to Codecov
-        uses: codecov/codecov-action@5a1091511ad55cbe89839c7260b706298ca349f7 # v5
+        uses: codecov/codecov-action@671740ac38dd9b0130fbe1cec585b89eea48d3de # v5
         with:
           token: ${{ secrets.CODECOV_TOKEN }}
           directory: ./frontend/coverage
diff --git a/.github/workflows/codeql.yml b/.github/workflows/codeql.yml
index 8194f3f0..2f36963f 100644
--- a/.github/workflows/codeql.yml
+++ b/.github/workflows/codeql.yml
@@ -34,7 +34,7 @@ jobs:
         uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6
 
       - name: Initialize CodeQL
-        uses: github/codeql-action/init@cf1bb45a277cb3c205638b2cd5c984db1c46a412 # v4
+        uses: github/codeql-action/init@1b168cd39490f61582a9beae412bb7057a6b2c4e # v4
         with:
           languages: ${{ matrix.language }}
 
@@ -45,9 +45,9 @@ jobs:
           go-version: '1.25.5'
 
       - name: Autobuild
-        uses: github/codeql-action/autobuild@cf1bb45a277cb3c205638b2cd5c984db1c46a412 # v4
+        uses: github/codeql-action/autobuild@1b168cd39490f61582a9beae412bb7057a6b2c4e # v4
 
       - name: Perform CodeQL Analysis
-        uses: github/codeql-action/analyze@cf1bb45a277cb3c205638b2cd5c984db1c46a412 # v4
+        uses: github/codeql-action/analyze@1b168cd39490f61582a9beae412bb7057a6b2c4e # v4
         with:
           category: "/language:${{ matrix.language }}"
diff --git a/.github/workflows/docker-build.yml b/.github/workflows/docker-build.yml
index 66bf4376..3235fc61 100644
--- a/.github/workflows/docker-build.yml
+++ b/.github/workflows/docker-build.yml
@@ -151,7 +151,7 @@ jobs:
 
       - name: Upload Trivy results
         if: github.event_name != 'pull_request' && steps.skip.outputs.skip_build != 'true' && steps.trivy-check.outputs.exists == 'true'
-        uses: github/codeql-action/upload-sarif@cf1bb45a277cb3c205638b2cd5c984db1c46a412 # v4.31.7
+        uses: github/codeql-action/upload-sarif@1b168cd39490f61582a9beae412bb7057a6b2c4e # v4.31.8
         with:
           sarif_file: 'trivy-results.sarif'
           token: ${{ secrets.GITHUB_TOKEN }}
diff --git a/.github/workflows/docker-publish.yml b/.github/workflows/docker-publish.yml
index c6aded05..f3837577 100644
--- a/.github/workflows/docker-publish.yml
+++ b/.github/workflows/docker-publish.yml
@@ -155,7 +155,7 @@ jobs:
 
       - name: Upload Trivy results
         if: github.event_name != 'pull_request' && steps.skip.outputs.skip_build != 'true' && steps.trivy-check.outputs.exists == 'true'
-        uses: github/codeql-action/upload-sarif@cf1bb45a277cb3c205638b2cd5c984db1c46a412 # v4.31.7
+        uses: github/codeql-action/upload-sarif@1b168cd39490f61582a9beae412bb7057a6b2c4e # v4.31.8
         with:
           sarif_file: 'trivy-results.sarif'
           token: ${{ secrets.GITHUB_TOKEN }}
diff --git a/.github/workflows/docs-to-issues.yml b/.github/workflows/docs-to-issues.yml
new file mode 100644
index 00000000..a69d2355
--- /dev/null
+++ b/.github/workflows/docs-to-issues.yml
@@ -0,0 +1,369 @@
+name: Convert Docs to Issues
+
+on:
+  push:
+    branches:
+      - main
+      - development
+    paths:
+      - 'docs/issues/**/*.md'
+      - '!docs/issues/created/**'
+      - '!docs/issues/_TEMPLATE.md'
+      - '!docs/issues/README.md'
+
+  # Allow manual trigger
+  workflow_dispatch:
+    inputs:
+      dry_run:
+        description: 'Dry run (no issues created)'
+        required: false
+        default: 'false'
+        type: boolean
+      file_path:
+        description: 'Specific file to process (optional)'
+        required: false
+        type: string
+
+permissions:
+  contents: write
+  issues: write
+  pull-requests: write
+
+jobs:
+  convert-docs:
+    name: Convert Markdown to Issues
+    runs-on: ubuntu-latest
+    if: github.actor != 'github-actions[bot]'
+
+    steps:
+      - name: Checkout repository
+        uses: actions/checkout@11bd71901bbe5b1630ceea73d27597364c9af683 # v4
+        with:
+          fetch-depth: 2
+
+      - name: Set up Node.js
+        uses: actions/setup-node@39370e3970a6d050c480ffad4ff0ed4d3fdee5af # v4
+        with:
+          node-version: '20'
+
+      - name: Install dependencies
+        run: npm install gray-matter
+
+      - name: Detect changed files
+        id: changes
+        uses: actions/github-script@60a0d83039c74a4aee543508d2ffcb1c3799cdea # v7
+        with:
+          script: |
+            const fs = require('fs');
+            const path = require('path');
+
+            // Manual file specification
+            const manualFile = '${{ github.event.inputs.file_path }}';
+            if (manualFile) {
+              if (fs.existsSync(manualFile)) {
+                core.setOutput('files', JSON.stringify([manualFile]));
+                return;
+              } else {
+                core.setFailed(`File not found: ${manualFile}`);
+                return;
+              }
+            }
+
+            // Get changed files from commit
+            const { data: commit } = await github.rest.repos.getCommit({
+              owner: context.repo.owner,
+              repo: context.repo.repo,
+              ref: context.sha
+            });
+
+            const changedFiles = (commit.files || [])
+              .filter(f => f.filename.startsWith('docs/issues/'))
+              .filter(f => !f.filename.startsWith('docs/issues/created/'))
+              .filter(f => !f.filename.includes('_TEMPLATE'))
+              .filter(f => !f.filename.includes('README'))
+              .filter(f => f.filename.endsWith('.md'))
+              .filter(f => f.status !== 'removed')
+              .map(f => f.filename);
+
+            console.log('Changed issue files:', changedFiles);
+            core.setOutput('files', JSON.stringify(changedFiles));
+
+      - name: Process issue files
+        id: process
+        uses: actions/github-script@60a0d83039c74a4aee543508d2ffcb1c3799cdea # v7
+        env:
+          DRY_RUN: ${{ github.event.inputs.dry_run || 'false' }}
+        with:
+          script: |
+            const fs = require('fs');
+            const path = require('path');
+            const matter = require('gray-matter');
+
+            const files = JSON.parse('${{ steps.changes.outputs.files }}');
+            const isDryRun = process.env.DRY_RUN === 'true';
+            const createdIssues = [];
+            const errors = [];
+
+            if (files.length === 0) {
+              console.log('No issue files to process');
+              core.setOutput('created_count', 0);
+              core.setOutput('created_issues', '[]');
+              core.setOutput('errors', '[]');
+              return;
+            }
+
+            // Label color map
+            const labelColors = {
+              testing: 'BFD4F2',
+              feature: 'A2EEEF',
+              enhancement: '84B6EB',
+              bug: 'D73A4A',
+              documentation: '0075CA',
+              backend: '1D76DB',
+              frontend: '5EBEFF',
+              security: 'EE0701',
+              ui: '7057FF',
+              caddy: '1F6FEB',
+              'needs-triage': 'FBCA04',
+              acl: 'C5DEF5',
+              regression: 'D93F0B',
+              'manual-testing': 'BFD4F2',
+              'bulk-acl': '006B75',
+              'error-handling': 'D93F0B',
+              'ui-ux': '7057FF',
+              integration: '0E8A16',
+              performance: 'EDEDED',
+              'cross-browser': '5319E7',
+              plus: 'FFD700',
+              beta: '0052CC',
+              alpha: '5319E7',
+              high: 'D93F0B',
+              medium: 'FBCA04',
+              low: '0E8A16',
+              critical: 'B60205',
+              architecture: '006B75',
+              database: '006B75',
+              'post-beta': '006B75'
+            };
+
+            // Helper: Ensure label exists
+            async function ensureLabel(name) {
+              try {
+                await github.rest.issues.getLabel({
+                  owner: context.repo.owner,
+                  repo: context.repo.repo,
+                  name: name
+                });
+              } catch (e) {
+                if (e.status === 404) {
+                  await github.rest.issues.createLabel({
+                    owner: context.repo.owner,
+                    repo: context.repo.repo,
+                    name: name,
+                    color: labelColors[name.toLowerCase()] || '666666'
+                  });
+                  console.log(`Created label: ${name}`);
+                }
+              }
+            }
+
+            // Helper: Parse markdown file
+            function parseIssueFile(filePath) {
+              const content = fs.readFileSync(filePath, 'utf8');
+              const { data: frontmatter, content: body } = matter(content);
+
+              // Extract title: frontmatter > first H1 > filename
+              let title = frontmatter.title;
+              if (!title) {
+                const h1Match = body.match(/^#\s+(.+)$/m);
+                title = h1Match ? h1Match[1] : path.basename(filePath, '.md').replace(/-/g, ' ');
+              }
+
+              // Build labels array
+              const labels = [...(frontmatter.labels || [])];
+              if (frontmatter.priority) labels.push(frontmatter.priority);
+              if (frontmatter.type) labels.push(frontmatter.type);
+
+              return {
+                title,
+                body: body.trim(),
+                labels: [...new Set(labels)],
+                assignees: frontmatter.assignees || [],
+                milestone: frontmatter.milestone,
+                parent_issue: frontmatter.parent_issue,
+                create_sub_issues: frontmatter.create_sub_issues || false
+              };
+            }
+
+            // Helper: Extract sub-issues from H2 sections
+            function extractSubIssues(body, parentLabels) {
+              const sections = [];
+              const lines = body.split('\n');
+              let currentSection = null;
+              let currentBody = [];
+
+              for (const line of lines) {
+                const h2Match = line.match(/^##\s+(?:Sub-Issue\s*#?\d*:?\s*)?(.+)$/);
+                if (h2Match) {
+                  if (currentSection) {
+                    sections.push({
+                      title: currentSection,
+                      body: currentBody.join('\n').trim(),
+                      labels: [...parentLabels]
+                    });
+                  }
+                  currentSection = h2Match[1].trim();
+                  currentBody = [];
+                } else if (currentSection) {
+                  currentBody.push(line);
+                }
+              }
+
+              if (currentSection) {
+                sections.push({
+                  title: currentSection,
+                  body: currentBody.join('\n').trim(),
+                  labels: [...parentLabels]
+                });
+              }
+
+              return sections;
+            }
+
+            // Process each file
+            for (const filePath of files) {
+              console.log(`\nProcessing: ${filePath}`);
+
+              try {
+                const parsed = parseIssueFile(filePath);
+                console.log(`  Title: ${parsed.title}`);
+                console.log(`  Labels: ${parsed.labels.join(', ')}`);
+
+                if (isDryRun) {
+                  console.log('  [DRY RUN] Would create issue');
+                  createdIssues.push({ file: filePath, title: parsed.title, dryRun: true });
+                  continue;
+                }
+
+                // Ensure labels exist
+                for (const label of parsed.labels) {
+                  await ensureLabel(label);
+                }
+
+                // Create the main issue
+                const issueBody = parsed.body +
+                  `\n\n---\n*Auto-created from [${path.basename(filePath)}](https://github.com/${context.repo.owner}/${context.repo.repo}/blob/${context.sha}/${filePath})*`;
+
+                const issueResponse = await github.rest.issues.create({
+                  owner: context.repo.owner,
+                  repo: context.repo.repo,
+                  title: parsed.title,
+                  body: issueBody,
+                  labels: parsed.labels,
+                  assignees: parsed.assignees
+                });
+
+                const issueNumber = issueResponse.data.number;
+                console.log(`  Created issue #${issueNumber}`);
+
+                // Handle sub-issues
+                if (parsed.create_sub_issues) {
+                  const subIssues = extractSubIssues(parsed.body, parsed.labels);
+                  for (const sub of subIssues) {
+                    for (const label of sub.labels) {
+                      await ensureLabel(label);
+                    }
+                    const subResponse = await github.rest.issues.create({
+                      owner: context.repo.owner,
+                      repo: context.repo.repo,
+                      title: `[${parsed.title}] ${sub.title}`,
+                      body: sub.body + `\n\n---\n*Sub-issue of #${issueNumber}*`,
+                      labels: sub.labels,
+                      assignees: parsed.assignees
+                    });
+                    console.log(`    Created sub-issue #${subResponse.data.number}: ${sub.title}`);
+                  }
+                }
+
+                // Link to parent issue if specified
+                if (parsed.parent_issue) {
+                  await github.rest.issues.createComment({
+                    owner: context.repo.owner,
+                    repo: context.repo.repo,
+                    issue_number: parsed.parent_issue,
+                    body: `Sub-issue created: #${issueNumber}`
+                  });
+                }
+
+                createdIssues.push({
+                  file: filePath,
+                  title: parsed.title,
+                  issueNumber
+                });
+
+              } catch (error) {
+                console.error(`  Error processing ${filePath}: ${error.message}`);
+                errors.push({ file: filePath, error: error.message });
+              }
+            }
+
+            core.setOutput('created_count', createdIssues.length);
+            core.setOutput('created_issues', JSON.stringify(createdIssues));
+            core.setOutput('errors', JSON.stringify(errors));
+
+            if (errors.length > 0) {
+              core.warning(`${errors.length} file(s) had errors`);
+            }
+
+      - name: Move processed files
+        if: steps.process.outputs.created_count != '0' && github.event.inputs.dry_run != 'true'
+        run: |
+          mkdir -p docs/issues/created
+          CREATED_ISSUES='${{ steps.process.outputs.created_issues }}'
+          echo "$CREATED_ISSUES" | jq -r '.[].file' | while read file; do
+            if [ -f "$file" ] && [ ! -z "$file" ]; then
+              filename=$(basename "$file")
+              timestamp=$(date +%Y%m%d)
+              mv "$file" "docs/issues/created/${timestamp}-${filename}"
+              echo "Moved: $file -> docs/issues/created/${timestamp}-${filename}"
+            fi
+          done
+
+      - name: Commit moved files
+        if: steps.process.outputs.created_count != '0' && github.event.inputs.dry_run != 'true'
+        run: |
+          git config --local user.email "github-actions[bot]@users.noreply.github.com"
+          git config --local user.name "github-actions[bot]"
+          git add docs/issues/
+          git diff --staged --quiet || git commit -m "chore: move processed issue files to created/ [skip ci]"
+          git push
+
+      - name: Summary
+        if: always()
+        run: |
+          echo "## Docs to Issues Summary" >> $GITHUB_STEP_SUMMARY
+          echo "" >> $GITHUB_STEP_SUMMARY
+
+          CREATED='${{ steps.process.outputs.created_issues }}'
+          ERRORS='${{ steps.process.outputs.errors }}'
+          DRY_RUN='${{ github.event.inputs.dry_run }}'
+
+          if [ "$DRY_RUN" = "true" ]; then
+            echo "🔍 **Dry Run Mode** - No issues were actually created" >> $GITHUB_STEP_SUMMARY
+            echo "" >> $GITHUB_STEP_SUMMARY
+          fi
+
+          echo "### Created Issues" >> $GITHUB_STEP_SUMMARY
+          if [ -n "$CREATED" ] && [ "$CREATED" != "[]" ] && [ "$CREATED" != "null" ]; then
+            echo "$CREATED" | jq -r '.[] | "- \(.title) (#\(.issueNumber // "dry-run"))"' >> $GITHUB_STEP_SUMMARY || echo "_Parse error_" >> $GITHUB_STEP_SUMMARY
+          else
+            echo "_No issues created_" >> $GITHUB_STEP_SUMMARY
+          fi
+
+          echo "" >> $GITHUB_STEP_SUMMARY
+          echo "### Errors" >> $GITHUB_STEP_SUMMARY
+          if [ -n "$ERRORS" ] && [ "$ERRORS" != "[]" ] && [ "$ERRORS" != "null" ]; then
+            echo "$ERRORS" | jq -r '.[] | "- ❌ \(.file): \(.error)"' >> $GITHUB_STEP_SUMMARY || echo "_Parse error_" >> $GITHUB_STEP_SUMMARY
+          else
+            echo "_No errors_" >> $GITHUB_STEP_SUMMARY
+          fi
diff --git a/.github/workflows/docs.yml b/.github/workflows/docs.yml
index 3e1366ec..97901097 100644
--- a/.github/workflows/docs.yml
+++ b/.github/workflows/docs.yml
@@ -35,7 +35,7 @@ jobs:
       - name: 🔧 Set up Node.js
         uses: actions/setup-node@395ad3262231945c25e8478fd5baf05154b1d79f # v6
         with:
-          node-version: '24.11.1'
+          node-version: '24.12.0'
 
       # Step 3: Create a beautiful docs site structure
       - name: 📝 Build documentation site
diff --git a/.github/workflows/propagate-changes.yml b/.github/workflows/propagate-changes.yml
index 1a193bc8..de3b3b4d 100644
--- a/.github/workflows/propagate-changes.yml
+++ b/.github/workflows/propagate-changes.yml
@@ -20,7 +20,7 @@ jobs:
       - name: Set up Node (for github-script)
         uses: actions/setup-node@395ad3262231945c25e8478fd5baf05154b1d79f # v6
         with:
-          node-version: '24.11.1'
+          node-version: '24.12.0'
 
       - name: Propagate Changes
         uses: actions/github-script@ed597411d8f924073f98dfc5c65a23a2325f34cd # v8
diff --git a/.github/workflows/quality-checks.yml b/.github/workflows/quality-checks.yml
index c2d98376..1b6ba5ee 100644
--- a/.github/workflows/quality-checks.yml
+++ b/.github/workflows/quality-checks.yml
@@ -89,7 +89,7 @@ jobs:
       - name: Set up Node.js
         uses: actions/setup-node@395ad3262231945c25e8478fd5baf05154b1d79f # v6.1.0
         with:
-          node-version: '24.11.1'
+          node-version: '24.12.0'
           cache: 'npm'
           cache-dependency-path: frontend/package-lock.json
 
diff --git a/.github/workflows/release-goreleaser.yml b/.github/workflows/release-goreleaser.yml
index c9068e89..d19f1329 100644
--- a/.github/workflows/release-goreleaser.yml
+++ b/.github/workflows/release-goreleaser.yml
@@ -31,7 +31,7 @@ jobs:
       - name: Set up Node.js
         uses: actions/setup-node@395ad3262231945c25e8478fd5baf05154b1d79f # v6
         with:
-          node-version: '24.11.1'
+          node-version: '24.12.0'
 
       - name: Build Frontend
         working-directory: frontend
diff --git a/.github/workflows/renovate.yml b/.github/workflows/renovate.yml
index eb3b5a36..efab03ed 100644
--- a/.github/workflows/renovate.yml
+++ b/.github/workflows/renovate.yml
@@ -37,7 +37,7 @@ jobs:
           fi
 
       - name: Run Renovate
-        uses: renovatebot/github-action@5712c6a41dea6cdf32c72d92a763bd417e6606aa # v44.0.5
+        uses: renovatebot/github-action@502904f1cefdd70cba026cb1cbd8c53a1443e91b # v44.1.0
         with:
           configurationFile: .github/renovate.json
           token: ${{ env.GITHUB_TOKEN }}
diff --git a/.github/workflows/repo-health.yml b/.github/workflows/repo-health.yml
index 462d2021..93d17dd6 100644
--- a/.github/workflows/repo-health.yml
+++ b/.github/workflows/repo-health.yml
@@ -32,7 +32,7 @@ jobs:
 
       - name: Upload health output
         if: always()
-        uses: actions/upload-artifact@330a01c490aca151604b8cf639adc76d48f6c5d4 # v5
+        uses: actions/upload-artifact@b7c566a772e6b6bfb58ed0dc250532a479d7789f # v6
         with:
           name: repo-health-output
           path: |
diff --git a/Dockerfile b/Dockerfile
index 5009e47d..e2f3ea38 100644
--- a/Dockerfile
+++ b/Dockerfile
@@ -25,7 +25,7 @@ FROM --platform=$BUILDPLATFORM tonistiigi/xx:1.9.0 AS xx
 
 # ---- Frontend Builder ----
 # Build the frontend using the BUILDPLATFORM to avoid arm64 musl Rollup native issues
-FROM --platform=$BUILDPLATFORM node:24.11.1-alpine AS frontend-builder
+FROM --platform=$BUILDPLATFORM node:24.12.0-alpine AS frontend-builder
 WORKDIR /app/frontend
 
 # Copy frontend package files
diff --git a/docs/issues/README.md b/docs/issues/README.md
new file mode 100644
index 00000000..41feb422
--- /dev/null
+++ b/docs/issues/README.md
@@ -0,0 +1,85 @@
+# docs/issues - Issue Specification Files
+
+This directory contains markdown files that are automatically converted to GitHub Issues when merged to `main` or `development`.
+
+## How It Works
+
+1. **Create a markdown file** in this directory using the template format
+2. **Add YAML frontmatter** with issue metadata (title, labels, priority, etc.)
+3. **Merge to main/development** - the `docs-to-issues.yml` workflow runs
+4. **GitHub Issue is created** with your specified metadata
+5. **File is moved** to `docs/issues/created/` to prevent duplicates
+
+## Quick Start
+
+Copy `_TEMPLATE.md` and fill in your issue details:
+
+```yaml
+---
+title: "My New Issue"
+labels:
+  - feature
+  - backend
+priority: medium
+---
+
+# My New Issue
+
+Description of the issue...
+```
+
+## Frontmatter Fields
+
+| Field | Required | Description |
+|-------|----------|-------------|
+| `title` | Yes* | Issue title (*or uses first H1 as fallback) |
+| `labels` | No | Array of labels to apply |
+| `priority` | No | `critical`, `high`, `medium`, `low` |
+| `milestone` | No | Milestone name |
+| `assignees` | No | Array of GitHub usernames |
+| `parent_issue` | No | Parent issue number for linking |
+| `create_sub_issues` | No | If `true`, each `## Section` becomes a sub-issue |
+
+## Sub-Issues
+
+To create multiple related issues from one file, set `create_sub_issues: true`:
+
+```yaml
+---
+title: "Main Testing Issue"
+labels: [testing]
+create_sub_issues: true
+---
+
+# Main Testing Issue
+
+Overview content for the parent issue.
+
+## Unit Testing
+
+This section becomes a separate issue.
+
+## Integration Testing
+
+This section becomes another separate issue.
+```
+
+## Manual Trigger
+
+You can manually run the workflow with:
+
+```bash
+# Dry run (no issues created)
+gh workflow run docs-to-issues.yml -f dry_run=true
+
+# Process specific file
+gh workflow run docs-to-issues.yml -f file_path=docs/issues/my-issue.md
+```
+
+## Labels
+
+Labels are automatically created if they don't exist. Common labels:
+
+- **Priority**: `critical`, `high`, `medium`, `low`
+- **Type**: `feature`, `bug`, `enhancement`, `testing`, `documentation`
+- **Component**: `backend`, `frontend`, `ui`, `security`, `caddy`, `database`
diff --git a/docs/issues/_TEMPLATE.md b/docs/issues/_TEMPLATE.md
new file mode 100644
index 00000000..462b79fd
--- /dev/null
+++ b/docs/issues/_TEMPLATE.md
@@ -0,0 +1,45 @@
+---
+# REQUIRED: Issue title
+title: "Your Issue Title"
+
+# OPTIONAL: Labels to apply (will be created if missing)
+labels:
+  - feature       # feature, bug, enhancement, testing, documentation
+  - backend       # backend, frontend, ui, security, caddy, database
+
+# OPTIONAL: Priority (creates matching label)
+priority: medium  # critical, high, medium, low
+
+# OPTIONAL: Milestone name
+milestone: "v0.2.0-beta.2"
+
+# OPTIONAL: GitHub usernames to assign
+assignees: []
+
+# OPTIONAL: Parent issue number for linking
+# parent_issue: 42
+
+# OPTIONAL: Parse ## sections as separate sub-issues
+# create_sub_issues: true
+---
+
+# Issue Title
+
+## Description
+
+Clear description of the issue or feature request.
+
+## Tasks
+
+- [ ] Task 1
+- [ ] Task 2
+- [ ] Task 3
+
+## Acceptance Criteria
+
+- [ ] Criterion 1
+- [ ] Criterion 2
+
+## Related Issues
+
+- #XX - Related issue description
diff --git a/docs/issues/created/.gitkeep b/docs/issues/created/.gitkeep
new file mode 100644
index 00000000..92e80370
--- /dev/null
+++ b/docs/issues/created/.gitkeep
@@ -0,0 +1 @@
+# Processed issue files are moved here after GitHub Issues are created
diff --git a/docs/issues/ACL-testing-tasks.md b/docs/issues/created/20251213-ACL-testing-tasks.md
similarity index 100%
rename from docs/issues/ACL-testing-tasks.md
rename to docs/issues/created/20251213-ACL-testing-tasks.md
diff --git a/docs/issues/Additional_Security.md b/docs/issues/created/20251213-Additional_Security.md
similarity index 100%
rename from docs/issues/Additional_Security.md
rename to docs/issues/created/20251213-Additional_Security.md
diff --git a/docs/issues/bulk-acl-subissues.md b/docs/issues/created/20251213-bulk-acl-subissues.md
similarity index 100%
rename from docs/issues/bulk-acl-subissues.md
rename to docs/issues/created/20251213-bulk-acl-subissues.md
diff --git a/docs/issues/bulk-acl-testing.md b/docs/issues/created/20251213-bulk-acl-testing.md
similarity index 100%
rename from docs/issues/bulk-acl-testing.md
rename to docs/issues/created/20251213-bulk-acl-testing.md
diff --git a/docs/issues/hectate.md b/docs/issues/created/20251213-hectate.md
similarity index 100%
rename from docs/issues/hectate.md
rename to docs/issues/created/20251213-hectate.md
diff --git a/docs/issues/orthrus.md b/docs/issues/created/20251213-orthrus.md
similarity index 100%
rename from docs/issues/orthrus.md
rename to docs/issues/created/20251213-orthrus.md
diff --git a/docs/issues/plex-remote-access-helper.md b/docs/issues/created/20251213-plex-remote-access-helper.md
similarity index 100%
rename from docs/issues/plex-remote-access-helper.md
rename to docs/issues/created/20251213-plex-remote-access-helper.md
diff --git a/docs/issues/rotating-loading-animations.md b/docs/issues/created/20251213-rotating-loading-animations.md
similarity index 100%
rename from docs/issues/rotating-loading-animations.md
rename to docs/issues/created/20251213-rotating-loading-animations.md
diff --git a/docs/plans/docs_to_issues_workflow.md b/docs/plans/docs_to_issues_workflow.md
new file mode 100644
index 00000000..3b3a96c4
--- /dev/null
+++ b/docs/plans/docs_to_issues_workflow.md
@@ -0,0 +1,910 @@
+# docs/issues to GitHub Issues Workflow - Implementation Plan
+
+**Version:** 1.0
+**Date:** 2025-12-13
+**Status:** 📋 PLANNING
+
+---
+
+## Executive Summary
+
+This document provides a comprehensive plan for a GitHub Actions workflow that automatically converts markdown files in `docs/issues/` into GitHub Issues, applies labels, and adds them to the project board.
+
+---
+
+## 1. Research Findings
+
+### 1.1 Current docs/issues File Analysis
+
+Analyzed 8 existing files in `docs/issues/`:
+
+| File | Structure | Has Frontmatter | Labels Present | Title Pattern |
+|------|-----------|-----------------|----------------|---------------|
+| `ACL-testing-tasks.md` | Free-form + metadata section | ❌ | Inline suggestion | H1 + metadata block |
+| `Additional_Security.md` | Markdown lists | ❌ | ❌ | H3 title |
+| `bulk-acl-subissues.md` | Multi-issue spec | ❌ | Inline per section | Inline titles |
+| `bulk-acl-testing.md` | Full issue template | ❌ | Inline section | H1 title |
+| `hectate.md` | Feature spec | ❌ | ❌ | H1 title |
+| `orthrus.md` | Feature spec | ❌ | ❌ | H1 title |
+| `plex-remote-access-helper.md` | Issue template | ❌ | Inline section | `## Issue Title` |
+| `rotating-loading-animations.md` | Enhancement spec | ❌ | `**Issue Type**` line | H1 title |
+
+**Key Finding:** No files use YAML frontmatter. Most have ad-hoc metadata embedded in markdown body.
+
+### 1.2 Existing Workflow Patterns
+
+From `.github/workflows/`:
+
+| Workflow | Pattern | Relevance |
+|----------|---------|-----------|
+| `auto-label-issues.yml` | `actions/github-script` for issue manipulation | Label creation, issue API |
+| `propagate-changes.yml` | Complex `github-script` with file analysis | File path detection |
+| `auto-add-to-project.yml` | `actions/add-to-project` action | Project board integration |
+| `create-labels.yml` | Label creation/update logic | Label management |
+
+### 1.3 Project Board Configuration
+
+- Project URL stored in `secrets.PROJECT_URL`
+- PAT token: `secrets.ADD_TO_PROJECT_PAT`
+- Uses `actions/add-to-project@v1.0.2` for automatic addition
+
+---
+
+## 2. Markdown File Format Specification
+
+### 2.1 Required Frontmatter Format
+
+All files in `docs/issues/` should use YAML frontmatter:
+
+```yaml
+---
+title: "Issue Title Here"
+labels:
+  - testing
+  - feature
+  - backend
+assignees:
+  - username1
+  - username2
+milestone: "v0.2.0-beta.2"
+priority: high          # critical, high, medium, low
+type: feature           # feature, bug, enhancement, testing, documentation
+parent_issue: 42        # Optional: Link as sub-issue
+create_sub_issues: true # Optional: Parse ## sections as separate issues
+---
+
+# Issue Title (H1 fallback if frontmatter title missing)
+
+Issue body content starts here...
+```
+
+### 2.2 Frontmatter Fields
+
+| Field | Required | Type | Description |
+|-------|----------|------|-------------|
+| `title` | Yes* | string | Issue title (*or H1 fallback) |
+| `labels` | No | array | Labels to apply (created if missing) |
+| `assignees` | No | array | GitHub usernames |
+| `milestone` | No | string | Milestone name |
+| `priority` | No | enum | Maps to priority label |
+| `type` | No | enum | Maps to type label |
+| `parent_issue` | No | number | Parent issue number for linking |
+| `create_sub_issues` | No | boolean | Parse H2 sections as sub-issues |
+
+### 2.3 Sub-Issue Detection
+
+When `create_sub_issues: true`, each `## Section Title` becomes a sub-issue:
+
+```markdown
+---
+title: "Main Testing Issue"
+labels: [testing]
+create_sub_issues: true
+---
+
+# Main Testing Issue
+
+Overview text (goes in parent issue).
+
+## Sub-Issue #1: Unit Testing
+
+This section becomes a separate issue titled "Unit Testing"
+with body content from this section.
+
+## Sub-Issue #2: Integration Testing
+
+This section becomes another separate issue.
+```
+
+---
+
+## 3. Workflow Implementation
+
+### 3.1 Workflow File: `.github/workflows/docs-to-issues.yml`
+
+```yaml
+name: Convert Docs to Issues
+
+on:
+  push:
+    branches:
+      - main
+      - development
+    paths:
+      - 'docs/issues/**/*.md'
+      - '!docs/issues/created/**'
+
+  # Allow manual trigger
+  workflow_dispatch:
+    inputs:
+      dry_run:
+        description: 'Dry run (no issues created)'
+        required: false
+        default: 'false'
+        type: boolean
+      file_path:
+        description: 'Specific file to process (optional)'
+        required: false
+        type: string
+
+permissions:
+  contents: write
+  issues: write
+  pull-requests: write
+
+jobs:
+  convert-docs:
+    name: Convert Markdown to Issues
+    runs-on: ubuntu-latest
+    if: github.actor != 'github-actions[bot]'
+
+    steps:
+      - name: Checkout repository
+        uses: actions/checkout@11bd71901bbe5b1630ceea73d27597364c9af683 # v4
+        with:
+          fetch-depth: 2  # Need previous commit for diff
+
+      - name: Set up Node.js
+        uses: actions/setup-node@39370e3970a6d050c480ffad4ff0ed4d3fdee5af # v4
+        with:
+          node-version: '20'
+
+      - name: Install dependencies
+        run: npm install gray-matter
+
+      - name: Detect changed files
+        id: changes
+        uses: actions/github-script@60a0d83039c74a4aee543508d2ffcb1c3799cdea # v7
+        with:
+          script: |
+            const fs = require('fs');
+            const path = require('path');
+
+            // Manual file specification
+            const manualFile = '${{ github.event.inputs.file_path }}';
+            if (manualFile) {
+              if (fs.existsSync(manualFile)) {
+                core.setOutput('files', JSON.stringify([manualFile]));
+                return;
+              } else {
+                core.setFailed(`File not found: ${manualFile}`);
+                return;
+              }
+            }
+
+            // Get changed files from commit
+            const { data: commit } = await github.rest.repos.getCommit({
+              owner: context.repo.owner,
+              repo: context.repo.repo,
+              ref: context.sha
+            });
+
+            const changedFiles = (commit.files || [])
+              .filter(f => f.filename.startsWith('docs/issues/'))
+              .filter(f => !f.filename.startsWith('docs/issues/created/'))
+              .filter(f => f.filename.endsWith('.md'))
+              .filter(f => f.status !== 'removed')
+              .map(f => f.filename);
+
+            console.log('Changed issue files:', changedFiles);
+            core.setOutput('files', JSON.stringify(changedFiles));
+
+      - name: Process issue files
+        id: process
+        uses: actions/github-script@60a0d83039c74a4aee543508d2ffcb1c3799cdea # v7
+        env:
+          DRY_RUN: ${{ github.event.inputs.dry_run || 'false' }}
+        with:
+          script: |
+            const fs = require('fs');
+            const path = require('path');
+            const matter = require('gray-matter');
+
+            const files = JSON.parse('${{ steps.changes.outputs.files }}');
+            const isDryRun = process.env.DRY_RUN === 'true';
+            const createdIssues = [];
+            const errors = [];
+
+            if (files.length === 0) {
+              console.log('No issue files to process');
+              core.setOutput('created_count', 0);
+              return;
+            }
+
+            // Helper: Ensure label exists
+            async function ensureLabel(name) {
+              try {
+                await github.rest.issues.getLabel({
+                  owner: context.repo.owner,
+                  repo: context.repo.repo,
+                  name: name
+                });
+              } catch (e) {
+                if (e.status === 404) {
+                  // Create label with default color
+                  const colors = {
+                    testing: 'BFD4F2',
+                    feature: 'A2EEEF',
+                    enhancement: '84B6EB',
+                    bug: 'D73A4A',
+                    documentation: '0075CA',
+                    backend: '1D76DB',
+                    frontend: '5EBEFF',
+                    security: 'EE0701',
+                    ui: '7057FF',
+                    caddy: '1F6FEB',
+                    'needs-triage': 'FBCA04',
+                    acl: 'C5DEF5',
+                    regression: 'D93F0B',
+                    'manual-testing': 'BFD4F2',
+                    'bulk-acl': '006B75',
+                    'error-handling': 'D93F0B',
+                    'ui-ux': '7057FF',
+                    integration: '0E8A16',
+                    performance: 'EDEDED',
+                    'cross-browser': '5319E7',
+                    plus: 'FFD700',
+                    beta: '0052CC',
+                    alpha: '5319E7',
+                    high: 'D93F0B',
+                    medium: 'FBCA04',
+                    low: '0E8A16',
+                    critical: 'B60205'
+                  };
+                  await github.rest.issues.createLabel({
+                    owner: context.repo.owner,
+                    repo: context.repo.repo,
+                    name: name,
+                    color: colors[name.toLowerCase()] || '666666'
+                  });
+                  console.log(`Created label: ${name}`);
+                }
+              }
+            }
+
+            // Helper: Parse markdown file
+            function parseIssueFile(filePath) {
+              const content = fs.readFileSync(filePath, 'utf8');
+              const { data: frontmatter, content: body } = matter(content);
+
+              // Extract title: frontmatter > first H1 > filename
+              let title = frontmatter.title;
+              if (!title) {
+                const h1Match = body.match(/^#\s+(.+)$/m);
+                title = h1Match ? h1Match[1] : path.basename(filePath, '.md');
+              }
+
+              // Build labels array
+              const labels = [...(frontmatter.labels || [])];
+              if (frontmatter.priority) labels.push(frontmatter.priority);
+              if (frontmatter.type) labels.push(frontmatter.type);
+
+              return {
+                title,
+                body: body.trim(),
+                labels: [...new Set(labels)],
+                assignees: frontmatter.assignees || [],
+                milestone: frontmatter.milestone,
+                parent_issue: frontmatter.parent_issue,
+                create_sub_issues: frontmatter.create_sub_issues || false
+              };
+            }
+
+            // Helper: Extract sub-issues from H2 sections
+            function extractSubIssues(body, parentLabels) {
+              const sections = [];
+              const regex = /^##\s+(?:Sub-Issue\s*#?\d*:?\s*)?(.+?)$([\s\S]*?)(?=^##\s|\Z)/gm;
+              let match;
+
+              while ((match = regex.exec(body)) !== null) {
+                const sectionTitle = match[1].trim();
+                const sectionBody = match[2].trim();
+
+                // Extract inline labels like **Labels**: `testing`, `acl`
+                const inlineLabels = [];
+                const labelMatch = sectionBody.match(/\*\*Labels?\*\*:?\s*[`']?([^`'\n]+)[`']?/i);
+                if (labelMatch) {
+                  labelMatch[1].split(',').forEach(l => {
+                    const label = l.replace(/[`']/g, '').trim();
+                    if (label) inlineLabels.push(label);
+                  });
+                }
+
+                sections.push({
+                  title: sectionTitle,
+                  body: sectionBody,
+                  labels: [...parentLabels, ...inlineLabels]
+                });
+              }
+
+              return sections;
+            }
+
+            // Process each file
+            for (const filePath of files) {
+              console.log(`\nProcessing: ${filePath}`);
+
+              try {
+                const parsed = parseIssueFile(filePath);
+                console.log(`  Title: ${parsed.title}`);
+                console.log(`  Labels: ${parsed.labels.join(', ')}`);
+
+                if (isDryRun) {
+                  console.log('  [DRY RUN] Would create issue');
+                  createdIssues.push({ file: filePath, title: parsed.title, dryRun: true });
+                  continue;
+                }
+
+                // Ensure labels exist
+                for (const label of parsed.labels) {
+                  await ensureLabel(label);
+                }
+
+                // Create the main issue
+                const issueResponse = await github.rest.issues.create({
+                  owner: context.repo.owner,
+                  repo: context.repo.repo,
+                  title: parsed.title,
+                  body: parsed.body + `\n\n---\n*Auto-created from [${path.basename(filePath)}](https://github.com/${context.repo.owner}/${context.repo.repo}/blob/${context.sha}/${filePath})*`,
+                  labels: parsed.labels,
+                  assignees: parsed.assignees
+                });
+
+                const issueNumber = issueResponse.data.number;
+                console.log(`  Created issue #${issueNumber}`);
+
+                // Handle sub-issues
+                if (parsed.create_sub_issues) {
+                  const subIssues = extractSubIssues(parsed.body, parsed.labels);
+                  for (const sub of subIssues) {
+                    for (const label of sub.labels) {
+                      await ensureLabel(label);
+                    }
+                    const subResponse = await github.rest.issues.create({
+                      owner: context.repo.owner,
+                      repo: context.repo.repo,
+                      title: `[${parsed.title}] ${sub.title}`,
+                      body: sub.body + `\n\n---\n*Sub-issue of #${issueNumber}*`,
+                      labels: sub.labels,
+                      assignees: parsed.assignees
+                    });
+                    console.log(`    Created sub-issue #${subResponse.data.number}: ${sub.title}`);
+                  }
+                }
+
+                // Link to parent issue if specified
+                if (parsed.parent_issue) {
+                  await github.rest.issues.createComment({
+                    owner: context.repo.owner,
+                    repo: context.repo.repo,
+                    issue_number: parsed.parent_issue,
+                    body: `Sub-issue created: #${issueNumber}`
+                  });
+                }
+
+                createdIssues.push({
+                  file: filePath,
+                  title: parsed.title,
+                  issueNumber
+                });
+
+              } catch (error) {
+                console.error(`  Error processing ${filePath}: ${error.message}`);
+                errors.push({ file: filePath, error: error.message });
+              }
+            }
+
+            core.setOutput('created_count', createdIssues.length);
+            core.setOutput('created_issues', JSON.stringify(createdIssues));
+            core.setOutput('errors', JSON.stringify(errors));
+
+            if (errors.length > 0) {
+              core.warning(`${errors.length} file(s) had errors`);
+            }
+
+      - name: Move processed files
+        if: steps.process.outputs.created_count != '0' && github.event.inputs.dry_run != 'true'
+        run: |
+          mkdir -p docs/issues/created
+          CREATED_ISSUES='${{ steps.process.outputs.created_issues }}'
+          echo "$CREATED_ISSUES" | jq -r '.[].file' | while read file; do
+            if [ -f "$file" ] && [ ! -z "$file" ]; then
+              filename=$(basename "$file")
+              timestamp=$(date +%Y%m%d)
+              mv "$file" "docs/issues/created/${timestamp}-${filename}"
+              echo "Moved: $file -> docs/issues/created/${timestamp}-${filename}"
+            fi
+          done
+
+      - name: Commit moved files
+        if: steps.process.outputs.created_count != '0' && github.event.inputs.dry_run != 'true'
+        run: |
+          git config --local user.email "github-actions[bot]@users.noreply.github.com"
+          git config --local user.name "github-actions[bot]"
+          git add docs/issues/
+          git diff --staged --quiet || git commit -m "chore: move processed issue files to created/ [skip ci]"
+          git push
+
+      - name: Add to project board
+        if: steps.process.outputs.created_count != '0' && github.event.inputs.dry_run != 'true'
+        continue-on-error: true
+        uses: actions/github-script@60a0d83039c74a4aee543508d2ffcb1c3799cdea # v7
+        env:
+          PROJECT_URL: ${{ secrets.PROJECT_URL }}
+          ADD_TO_PROJECT_PAT: ${{ secrets.ADD_TO_PROJECT_PAT }}
+        with:
+          github-token: ${{ secrets.ADD_TO_PROJECT_PAT || secrets.GITHUB_TOKEN }}
+          script: |
+            const projectUrl = process.env.PROJECT_URL;
+            if (!projectUrl) {
+              console.log('PROJECT_URL not configured, skipping project board');
+              return;
+            }
+
+            const createdIssues = JSON.parse('${{ steps.process.outputs.created_issues }}');
+            console.log(`Would add ${createdIssues.length} issues to project board`);
+            // Note: Actual project board integration requires GraphQL API
+            // The actions/add-to-project action handles this automatically
+            // for issues created via normal flow
+
+      - name: Summary
+        if: always()
+        run: |
+          echo "## Docs to Issues Summary" >> $GITHUB_STEP_SUMMARY
+          echo "" >> $GITHUB_STEP_SUMMARY
+
+          CREATED='${{ steps.process.outputs.created_issues }}'
+          ERRORS='${{ steps.process.outputs.errors }}'
+          DRY_RUN='${{ github.event.inputs.dry_run }}'
+
+          if [ "$DRY_RUN" = "true" ]; then
+            echo "🔍 **Dry Run Mode** - No issues were actually created" >> $GITHUB_STEP_SUMMARY
+            echo "" >> $GITHUB_STEP_SUMMARY
+          fi
+
+          echo "### Created Issues" >> $GITHUB_STEP_SUMMARY
+          if [ -n "$CREATED" ] && [ "$CREATED" != "[]" ]; then
+            echo "$CREATED" | jq -r '.[] | "- \(.title) (#\(.issueNumber // "dry-run"))"' >> $GITHUB_STEP_SUMMARY
+          else
+            echo "_No issues created_" >> $GITHUB_STEP_SUMMARY
+          fi
+
+          echo "" >> $GITHUB_STEP_SUMMARY
+          echo "### Errors" >> $GITHUB_STEP_SUMMARY
+          if [ -n "$ERRORS" ] && [ "$ERRORS" != "[]" ]; then
+            echo "$ERRORS" | jq -r '.[] | "- ❌ \(.file): \(.error)"' >> $GITHUB_STEP_SUMMARY
+          else
+            echo "_No errors_" >> $GITHUB_STEP_SUMMARY
+          fi
+```
+
+---
+
+## 4. File Conversion Templates
+
+### 4.1 Updated ACL-testing-tasks.md (Example)
+
+```yaml
+---
+title: "ACL: Test and validate ACL changes (feature/beta-release)"
+labels:
+  - testing
+  - needs-triage
+  - acl
+  - regression
+priority: high
+milestone: "v0.2.0-beta.2"
+create_sub_issues: false
+---
+
+# ACL: Test and validate ACL changes (feature/beta-release)
+
+**Repository:** Wikid82/Charon
+**Branch:** feature/beta-release
+
+## Purpose
+
+Create a tracked issue and sub-tasks to validate ACL-related changes...
+
+[rest of content unchanged]
+```
+
+### 4.2 Updated bulk-acl-subissues.md (Example with Sub-Issues)
+
+```yaml
+---
+title: "Bulk ACL Testing - Sub-Issues"
+labels:
+  - testing
+  - manual-testing
+  - bulk-acl
+priority: medium
+milestone: "v0.2.0-beta.2"
+create_sub_issues: true
+---
+
+# Bulk ACL Testing - Sub-Issues
+
+## Basic Functionality Testing
+
+**Labels**: `testing`, `manual-testing`, `bulk-acl`
+
+Test the core functionality of the bulk ACL feature...
+
+## ACL Removal Testing
+
+**Labels**: `testing`, `manual-testing`, `bulk-acl`
+
+Test the ability to remove access lists...
+
+[each ## section becomes a sub-issue]
+```
+
+### 4.3 Template for New Issue Files
+
+Create `docs/issues/_TEMPLATE.md`:
+
+```yaml
+---
+# REQUIRED: Issue title
+title: "Your Issue Title"
+
+# OPTIONAL: Labels to apply (will be created if missing)
+labels:
+  - feature       # feature, bug, enhancement, testing, documentation
+  - backend       # backend, frontend, ui, security, caddy, database
+
+# OPTIONAL: Priority (creates matching label)
+priority: medium  # critical, high, medium, low
+
+# OPTIONAL: Milestone name
+milestone: "v0.2.0-beta.2"
+
+# OPTIONAL: GitHub usernames to assign
+assignees: []
+
+# OPTIONAL: Parent issue number for linking
+# parent_issue: 42
+
+# OPTIONAL: Parse ## sections as separate sub-issues
+# create_sub_issues: true
+---
+
+# Issue Title
+
+## Description
+
+Clear description of the issue or feature request.
+
+## Tasks
+
+- [ ] Task 1
+- [ ] Task 2
+- [ ] Task 3
+
+## Acceptance Criteria
+
+- [ ] Criterion 1
+- [ ] Criterion 2
+
+## Related Issues
+
+- #XX - Related issue description
+
+---
+
+*Issue specification created: YYYY-MM-DD*
+```
+
+---
+
+## 5. Files to Update
+
+### 5.1 Existing docs/issues Files Needing Frontmatter
+
+| File | Action Needed |
+|------|---------------|
+| `ACL-testing-tasks.md` | Add frontmatter with extracted metadata |
+| `Additional_Security.md` | Add frontmatter, convert to issue format |
+| `bulk-acl-subissues.md` | Add frontmatter with `create_sub_issues: true` |
+| `bulk-acl-testing.md` | Add frontmatter with extracted metadata |
+| `hectate.md` | Add frontmatter (feature spec) |
+| `orthrus.md` | Add frontmatter (feature spec) |
+| `plex-remote-access-helper.md` | Add frontmatter, already has metadata section |
+| `rotating-loading-animations.md` | Add frontmatter, extract inline metadata |
+
+### 5.2 New Files to Create
+
+| File | Purpose |
+|------|---------|
+| `.github/workflows/docs-to-issues.yml` | Main workflow |
+| `docs/issues/_TEMPLATE.md` | Template for new issues |
+| `docs/issues/created/.gitkeep` | Directory for processed files |
+| `docs/issues/README.md` | Documentation for contributors |
+
+---
+
+## 6. Directory Structure
+
+```
+docs/
+├── issues/
+│   ├── README.md                    # How to create issue files
+│   ├── _TEMPLATE.md                 # Template for new issues
+│   ├── created/                     # Processed files moved here
+│   │   └── .gitkeep
+│   ├── ACL-testing-tasks.md         # Pending (needs frontmatter)
+│   ├── Additional_Security.md       # Pending
+│   ├── bulk-acl-subissues.md        # Pending
+│   └── ...
+```
+
+---
+
+## 7. Duplicate Prevention Strategy
+
+### 7.1 File-Based Tracking
+
+- **Processed files move to `docs/issues/created/`** with timestamp prefix
+- **Workflow excludes `created/` directory** from processing
+- **Git history provides audit trail** of when files were converted
+
+### 7.2 Issue Tracking
+
+Each created issue includes footer:
+```markdown
+---
+*Auto-created from [filename.md](link-to-source-commit)*
+```
+
+### 7.3 Manual Override
+
+- Use `workflow_dispatch` with specific file path to reprocess
+- Files in `created/` can be moved back for reprocessing
+
+---
+
+## 8. Project Board Integration
+
+### 8.1 Automatic Addition
+
+The workflow leverages the existing `auto-add-to-project.yml` which triggers on `issues: [opened]`.
+
+When the workflow creates an issue, the auto-add workflow automatically adds it to the project board (if `PROJECT_URL` secret is configured).
+
+### 8.2 Manual Configuration
+
+If not using `auto-add-to-project.yml`, configure in the docs-to-issues workflow:
+
+```yaml
+- name: Add to project
+  uses: actions/add-to-project@244f685bbc3b7adfa8466e08b698b5577571133e # v1.0.2
+  with:
+    project-url: ${{ secrets.PROJECT_URL }}
+    github-token: ${{ secrets.ADD_TO_PROJECT_PAT }}
+```
+
+---
+
+## 9. Testing Strategy
+
+### 9.1 Dry Run Testing
+
+```bash
+# Manually trigger with dry_run=true
+gh workflow run docs-to-issues.yml -f dry_run=true
+
+# Test specific file
+gh workflow run docs-to-issues.yml -f dry_run=true -f file_path=docs/issues/ACL-testing-tasks.md
+```
+
+### 9.2 Local Testing
+
+```bash
+# Parse frontmatter locally
+node -e "
+const matter = require('gray-matter');
+const fs = require('fs');
+const result = matter(fs.readFileSync('docs/issues/ACL-testing-tasks.md', 'utf8'));
+console.log(JSON.stringify(result.data, null, 2));
+"
+```
+
+### 9.3 Validation Checklist
+
+- [ ] Frontmatter parses correctly for all files
+- [ ] Labels are created when missing
+- [ ] Issue titles are correct
+- [ ] Issue bodies include full content
+- [ ] Sub-issues are created correctly (if `create_sub_issues: true`)
+- [ ] Files move to `created/` after processing
+- [ ] Auto-add-to-project triggers for new issues
+- [ ] Commit message includes `[skip ci]` to prevent loops
+
+---
+
+## 10. Implementation Phases
+
+### Phase 1: Setup (15 min)
+1. Create `.github/workflows/docs-to-issues.yml`
+2. Create `docs/issues/created/.gitkeep`
+3. Create `docs/issues/_TEMPLATE.md`
+4. Create `docs/issues/README.md`
+
+### Phase 2: File Migration (30 min)
+1. Add frontmatter to existing files (in order of priority)
+2. Test with dry_run mode
+3. Create one test issue to verify
+
+### Phase 3: Validation (15 min)
+1. Verify issue creation
+2. Verify label creation
+3. Verify project board integration
+4. Verify file move to `created/`
+
+---
+
+## 11. Risk Assessment
+
+| Risk | Impact | Mitigation |
+|------|--------|------------|
+| Duplicate issues | Low | File move + exclude pattern |
+| Label spam | Low | Predefined color map |
+| Rate limiting | Medium | Process files sequentially |
+| Malformed frontmatter | Medium | Try-catch with error logging |
+| Project board auth failure | Low | `continue-on-error: true` |
+
+---
+
+## 12. Definition of Done
+
+- [ ] Workflow file created and committed
+- [ ] All existing docs/issues files have valid frontmatter
+- [ ] Dry run succeeds with no errors
+- [ ] At least one test issue created successfully
+- [ ] File moved to `created/` after processing
+- [ ] Labels created automatically
+- [ ] Project board integration verified (if configured)
+- [ ] Documentation in `docs/issues/README.md`
+
+---
+
+## Appendix A: Label Color Reference
+
+```javascript
+const labelColors = {
+  // Priority
+  critical: 'B60205',
+  high: 'D93F0B',
+  medium: 'FBCA04',
+  low: '0E8A16',
+
+  // Milestone
+  alpha: '5319E7',
+  beta: '0052CC',
+  'post-beta': '006B75',
+
+  // Type
+  feature: 'A2EEEF',
+  bug: 'D73A4A',
+  enhancement: '84B6EB',
+  documentation: '0075CA',
+  testing: 'BFD4F2',
+
+  // Component
+  backend: '1D76DB',
+  frontend: '5EBEFF',
+  ui: '7057FF',
+  security: 'EE0701',
+  caddy: '1F6FEB',
+  database: '006B75',
+
+  // Custom
+  'needs-triage': 'FBCA04',
+  acl: 'C5DEF5',
+  'bulk-acl': '006B75',
+  'manual-testing': 'BFD4F2',
+  regression: 'D93F0B',
+  plus: 'FFD700'
+};
+```
+
+---
+
+## Appendix B: Frontmatter Conversion Examples
+
+### B.1 hectate.md (Feature Spec)
+
+```yaml
+---
+title: "Hecate: Tunnel & Pathway Manager"
+labels:
+  - feature
+  - backend
+  - architecture
+priority: medium
+milestone: "post-beta"
+type: feature
+---
+```
+
+### B.2 orthrus.md (Feature Spec)
+
+```yaml
+---
+title: "Orthrus: Remote Socket Proxy Agent"
+labels:
+  - feature
+  - backend
+  - architecture
+priority: medium
+milestone: "post-beta"
+type: feature
+---
+```
+
+### B.3 plex-remote-access-helper.md
+
+```yaml
+---
+title: "Plex Remote Access Helper & CGNAT Solver"
+labels:
+  - beta
+  - feature
+  - plus
+  - ui
+  - caddy
+priority: medium
+milestone: "beta"
+type: feature
+parent_issue: 44
+---
+```
+
+### B.4 rotating-loading-animations.md
+
+```yaml
+---
+title: "Enhancement: Rotating Thematic Loading Animations"
+labels:
+  - enhancement
+  - frontend
+  - ui
+priority: low
+type: enhancement
+---
+```
+
+### B.5 Additional_Security.md
+
+```yaml
+---
+title: "Additional Security Threats to Consider"
+labels:
+  - security
+  - documentation
+  - architecture
+priority: medium
+type: documentation
+---
+```
diff --git a/frontend/package-lock.json b/frontend/package-lock.json
index 6e44bac1..87c51ac1 100644
--- a/frontend/package-lock.json
+++ b/frontend/package-lock.json
@@ -12,9 +12,9 @@
         "axios": "^1.13.2",
         "clsx": "^2.1.1",
         "date-fns": "^4.1.0",
-        "lucide-react": "^0.556.0",
-        "react": "^19.2.1",
-        "react-dom": "^19.2.1",
+        "lucide-react": "^0.561.0",
+        "react": "^19.2.3",
+        "react-dom": "^19.2.3",
         "react-hook-form": "^7.68.0",
         "react-hot-toast": "^2.6.0",
         "react-router-dom": "^7.10.1",
@@ -23,7 +23,7 @@
       },
       "devDependencies": {
         "@playwright/test": "^1.57.0",
-        "@tailwindcss/postcss": "^4.1.17",
+        "@tailwindcss/postcss": "^4.1.18",
         "@testing-library/jest-dom": "^6.9.1",
         "@testing-library/react": "^16.3.0",
         "@testing-library/user-event": "^14.6.1",
@@ -36,13 +36,13 @@
         "@vitest/coverage-v8": "^4.0.15",
         "@vitest/ui": "^4.0.15",
         "autoprefixer": "^10.4.22",
-        "eslint": "^9.39.1",
+        "eslint": "^9.39.2",
         "eslint-plugin-react-hooks": "^7.0.1",
         "eslint-plugin-react-refresh": "^0.4.24",
         "jsdom": "^27.3.0",
-        "knip": "^5.72.0",
+        "knip": "^5.73.4",
         "postcss": "^8.5.6",
-        "tailwindcss": "^4.1.17",
+        "tailwindcss": "^4.1.18",
         "typescript": "^5.9.3",
         "typescript-eslint": "^8.49.0",
         "vite": "^7.2.7",
@@ -1186,10 +1186,11 @@
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     },
     "node_modules/@eslint/js": {
-      "version": "9.39.1",
-      "resolved": "https://registry.npmjs.org/@eslint/js/-/js-9.39.1.tgz",
-      "integrity": "sha512-S26Stp4zCy88tH94QbBv3XCuzRQiZ9yXofEILmglYTh/Ug/a9/umqvgFtYBAo3Lp0nsI/5/qH1CCrbdK3AP1Tw==",
+      "version": "9.39.2",
+      "resolved": "https://registry.npmjs.org/@eslint/js/-/js-9.39.2.tgz",
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       "dev": true,
+      "license": "MIT",
       "engines": {
         "node": "^18.18.0 || ^20.9.0 || >=21.1.0"
       },
@@ -1998,10 +1999,11 @@
       "dev": true
     },
     "node_modules/@tailwindcss/node": {
-      "version": "4.1.17",
-      "resolved": "https://registry.npmjs.org/@tailwindcss/node/-/node-4.1.17.tgz",
-      "integrity": "sha512-csIkHIgLb3JisEFQ0vxr2Y57GUNYh447C8xzwj89U/8fdW8LhProdxvnVH6U8M2Y73QKiTIH+LWbK3V2BBZsAg==",
+      "version": "4.1.18",
+      "resolved": "https://registry.npmjs.org/@tailwindcss/node/-/node-4.1.18.tgz",
+      "integrity": "sha512-DoR7U1P7iYhw16qJ49fgXUlry1t4CpXeErJHnQ44JgTSKMaZUdf17cfn5mHchfJ4KRBZRFA/Coo+MUF5+gOaCQ==",
       "dev": true,
+      "license": "MIT",
       "dependencies": {
         "@jridgewell/remapping": "^2.3.4",
         "enhanced-resolve": "^5.18.3",
@@ -2009,40 +2011,42 @@
         "lightningcss": "1.30.2",
         "magic-string": "^0.30.21",
         "source-map-js": "^1.2.1",
-        "tailwindcss": "4.1.17"
+        "tailwindcss": "4.1.18"
       }
     },
     "node_modules/@tailwindcss/oxide": {
-      "version": "4.1.17",
-      "resolved": "https://registry.npmjs.org/@tailwindcss/oxide/-/oxide-4.1.17.tgz",
-      "integrity": "sha512-F0F7d01fmkQhsTjXezGBLdrl1KresJTcI3DB8EkScCldyKp3Msz4hub4uyYaVnk88BAS1g5DQjjF6F5qczheLA==",
+      "version": "4.1.18",
+      "resolved": "https://registry.npmjs.org/@tailwindcss/oxide/-/oxide-4.1.18.tgz",
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       "dev": true,
+      "license": "MIT",
       "engines": {
         "node": ">= 10"
       },
       "optionalDependencies": {
-        "@tailwindcss/oxide-android-arm64": "4.1.17",
-        "@tailwindcss/oxide-darwin-arm64": "4.1.17",
-        "@tailwindcss/oxide-darwin-x64": "4.1.17",
-        "@tailwindcss/oxide-freebsd-x64": "4.1.17",
-        "@tailwindcss/oxide-linux-arm-gnueabihf": "4.1.17",
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-        "@tailwindcss/oxide-linux-x64-musl": "4.1.17",
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-        "@tailwindcss/oxide-win32-arm64-msvc": "4.1.17",
-        "@tailwindcss/oxide-win32-x64-msvc": "4.1.17"
+        "@tailwindcss/oxide-android-arm64": "4.1.18",
+        "@tailwindcss/oxide-darwin-arm64": "4.1.18",
+        "@tailwindcss/oxide-darwin-x64": "4.1.18",
+        "@tailwindcss/oxide-freebsd-x64": "4.1.18",
+        "@tailwindcss/oxide-linux-arm-gnueabihf": "4.1.18",
+        "@tailwindcss/oxide-linux-arm64-gnu": "4.1.18",
+        "@tailwindcss/oxide-linux-arm64-musl": "4.1.18",
+        "@tailwindcss/oxide-linux-x64-gnu": "4.1.18",
+        "@tailwindcss/oxide-linux-x64-musl": "4.1.18",
+        "@tailwindcss/oxide-wasm32-wasi": "4.1.18",
+        "@tailwindcss/oxide-win32-arm64-msvc": "4.1.18",
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+      "resolved": "https://registry.npmjs.org/@tailwindcss/oxide-android-arm64/-/oxide-android-arm64-4.1.18.tgz",
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       "cpu": [
         "arm64"
       ],
       "dev": true,
+      "license": "MIT",
       "optional": true,
       "os": [
         "android"
@@ -2052,13 +2056,14 @@
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+      "resolved": "https://registry.npmjs.org/@tailwindcss/oxide-darwin-arm64/-/oxide-darwin-arm64-4.1.18.tgz",
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       "cpu": [
         "arm64"
       ],
       "dev": true,
+      "license": "MIT",
       "optional": true,
       "os": [
         "darwin"
@@ -2068,13 +2073,14 @@
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+      "resolved": "https://registry.npmjs.org/@tailwindcss/oxide-darwin-x64/-/oxide-darwin-x64-4.1.18.tgz",
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       "cpu": [
         "x64"
       ],
       "dev": true,
+      "license": "MIT",
       "optional": true,
       "os": [
         "darwin"
@@ -2084,13 +2090,14 @@
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-      "resolved": "https://registry.npmjs.org/@tailwindcss/oxide-freebsd-x64/-/oxide-freebsd-x64-4.1.17.tgz",
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+      "resolved": "https://registry.npmjs.org/@tailwindcss/oxide-freebsd-x64/-/oxide-freebsd-x64-4.1.18.tgz",
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       "cpu": [
         "x64"
       ],
       "dev": true,
+      "license": "MIT",
       "optional": true,
       "os": [
         "freebsd"
@@ -2100,13 +2107,14 @@
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-      "resolved": "https://registry.npmjs.org/@tailwindcss/oxide-linux-arm-gnueabihf/-/oxide-linux-arm-gnueabihf-4.1.17.tgz",
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+      "resolved": "https://registry.npmjs.org/@tailwindcss/oxide-linux-arm-gnueabihf/-/oxide-linux-arm-gnueabihf-4.1.18.tgz",
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       "cpu": [
         "arm"
       ],
       "dev": true,
+      "license": "MIT",
       "optional": true,
       "os": [
         "linux"
@@ -2116,13 +2124,14 @@
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-      "resolved": "https://registry.npmjs.org/@tailwindcss/oxide-linux-arm64-gnu/-/oxide-linux-arm64-gnu-4.1.17.tgz",
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+      "resolved": "https://registry.npmjs.org/@tailwindcss/oxide-linux-arm64-gnu/-/oxide-linux-arm64-gnu-4.1.18.tgz",
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       "cpu": [
         "arm64"
       ],
       "dev": true,
+      "license": "MIT",
       "optional": true,
       "os": [
         "linux"
@@ -2132,13 +2141,14 @@
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-      "resolved": "https://registry.npmjs.org/@tailwindcss/oxide-linux-arm64-musl/-/oxide-linux-arm64-musl-4.1.17.tgz",
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+      "version": "4.1.18",
+      "resolved": "https://registry.npmjs.org/@tailwindcss/oxide-linux-arm64-musl/-/oxide-linux-arm64-musl-4.1.18.tgz",
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       "cpu": [
         "arm64"
       ],
       "dev": true,
+      "license": "MIT",
       "optional": true,
       "os": [
         "linux"
@@ -2148,13 +2158,14 @@
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     "node_modules/@tailwindcss/oxide-linux-x64-gnu": {
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@@ -2285,13 +2299,14 @@
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@@ -2301,16 +2316,17 @@
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@@ -3644,9 +3660,9 @@
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@@ -5498,9 +5514,9 @@
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@@ -5508,16 +5524,16 @@
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@@ -5883,9 +5899,9 @@
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diff --git a/frontend/package.json b/frontend/package.json
index 1af556c5..260b0f46 100644
--- a/frontend/package.json
+++ b/frontend/package.json
@@ -32,9 +32,9 @@
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-    "react": "^19.2.1",
-    "react-dom": "^19.2.1",
+    "lucide-react": "^0.561.0",
+    "react": "^19.2.3",
+    "react-dom": "^19.2.3",
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     "react-hot-toast": "^2.6.0",
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@@ -43,7 +43,7 @@
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@@ -57,13 +57,13 @@
 
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