diff --git a/web-ui/src/app/cases/[caseNumber]/page.tsx b/web-ui/src/app/cases/[caseNumber]/page.tsx
index 60c5165..7573f81 100644
--- a/web-ui/src/app/cases/[caseNumber]/page.tsx
+++ b/web-ui/src/app/cases/[caseNumber]/page.tsx
@@ -16,7 +16,9 @@ import { DocumentsPanel } from "@/components/cases/documents-panel";
 import { DraftsPanel } from "@/components/cases/drafts-panel";
 import { UploadSheet } from "@/components/documents/upload-sheet";
 import { expectedOutcomes } from "@/lib/schemas/case";
-import { useCase } from "@/lib/api/cases";
+import { useCase, useStartWorkflow } from "@/lib/api/cases";
+import { toast } from "sonner";
+import { Play, Loader2 } from "lucide-react";
 
 const EXPECTED_OUTCOME_LABELS: Record<string, string> = Object.fromEntries(
   expectedOutcomes.map((o) => [o.value, o.label]),
@@ -33,6 +35,8 @@ export default function CaseDetailPage({
 }) {
   const { caseNumber } = use(params);
   const { data, isPending, error } = useCase(caseNumber);
+  const startWorkflow = useStartWorkflow(caseNumber);
+  const canStartWorkflow = data?.status === "new" || data?.status === "documents_ready";
   const expectedOutcomeLabel = data?.expected_outcome
     ? EXPECTED_OUTCOME_LABELS[data.expected_outcome] ?? data.expected_outcome
     : null;
@@ -107,6 +111,29 @@ export default function CaseDetailPage({
                         </dl>
                       </div>
                       <div className="flex items-center gap-3 flex-wrap pt-2 border-t border-rule">
+                        {canStartWorkflow && (
+                          <Button
+                            className="bg-gold-deep hover:bg-gold-deep/90 text-parchment"
+                            disabled={startWorkflow.isPending}
+                            onClick={() =>
+                              startWorkflow.mutate(undefined, {
+                                onSuccess: (res) =>
+                                  toast.success(
+                                    `תהליך הופעל — ${res.issue_identifier}`,
+                                  ),
+                                onError: (err) =>
+                                  toast.error(`שגיאה: ${err.message}`),
+                              })
+                            }
+                          >
+                            {startWorkflow.isPending ? (
+                              <Loader2 className="w-4 h-4 animate-spin me-1.5" />
+                            ) : (
+                              <Play className="w-4 h-4 me-1.5" />
+                            )}
+                            התחל תהליך
+                          </Button>
+                        )}
                         <Button asChild className="bg-navy hover:bg-navy-soft text-parchment">
                           <Link href={`/cases/${caseNumber}/compose`}>
                             פתח בעורך ההחלטה
diff --git a/web-ui/src/lib/api/cases.ts b/web-ui/src/lib/api/cases.ts
index 5463ca2..458cd7c 100644
--- a/web-ui/src/lib/api/cases.ts
+++ b/web-ui/src/lib/api/cases.ts
@@ -167,6 +167,32 @@ export function useGitStatus(caseNumber: string | undefined) {
   });
 }
 
+export type StartWorkflowResult = {
+  case_number: string;
+  status: string;
+  issue_id: string;
+  issue_identifier: string;
+  project_url: string;
+  wakeup: Record<string, unknown>;
+};
+
+export function useStartWorkflow(caseNumber: string | undefined) {
+  const qc = useQueryClient();
+  return useMutation({
+    mutationFn: () =>
+      apiRequest<StartWorkflowResult>(
+        `/api/cases/${caseNumber}/start-workflow`,
+        { method: "POST" },
+      ),
+    onSuccess: () => {
+      qc.invalidateQueries({ queryKey: casesKeys.all });
+      if (caseNumber) {
+        qc.invalidateQueries({ queryKey: casesKeys.detail(caseNumber) });
+      }
+    },
+  });
+}
+
 export function useWorkflowStatus(caseNumber: string | undefined) {
   return useQuery({
     queryKey: [...casesKeys.all, "workflow", caseNumber ?? ""] as const,
diff --git a/web/app.py b/web/app.py
index eea03d0..d2f5311 100644
--- a/web/app.py
+++ b/web/app.py
@@ -35,7 +35,12 @@ from legal_mcp.tools import cases as cases_tools, search as search_tools, workfl
 _web_dir = Path(__file__).resolve().parent
 sys.path.insert(0, str(_web_dir.parent))
 from web.gitea_client import create_repo, setup_remote_and_push
-from web.paperclip_client import create_project as pc_create_project, get_project_url
+from web.paperclip_client import (
+    create_project as pc_create_project,
+    create_workflow_issue as pc_create_workflow_issue,
+    get_project_url,
+    wake_ceo_agent as pc_wake_ceo,
+)
 
 
 logger = logging.getLogger(__name__)
@@ -1129,7 +1134,16 @@ async def api_case_git_status(case_number: str):
     if not git_dir.exists():
         return {"synced": False, "error": "no_repo"}
 
-    env = {"PATH": os.environ.get("PATH", "/usr/bin:/bin"), "GIT_TERMINAL_PROMPT": "0"}
+    env = {
+        "PATH": os.environ.get("PATH", "/usr/bin:/bin"),
+        "HOME": os.environ.get("HOME", "/root"),
+        "GIT_TERMINAL_PROMPT": "0",
+        "GIT_CONFIG_GLOBAL": "/dev/null",
+    }
+    # Ensure git trusts the case directory regardless of ownership
+    env["GIT_CONFIG_COUNT"] = "1"
+    env["GIT_CONFIG_KEY_0"] = "safe.directory"
+    env["GIT_CONFIG_VALUE_0"] = str(case_dir)
 
     # Last commit info
     log = subprocess.run(
@@ -2160,6 +2174,55 @@ async def api_paperclip_create_project(req: PaperclipProjectRequest):
     return project
 
 
+@app.post("/api/cases/{case_number}/start-workflow")
+async def api_start_workflow(case_number: str):
+    """Start the CEO agent workflow for a case.
+
+    Creates a workflow issue in Paperclip and wakes the CEO agent.
+    Only works when case status is 'new' or 'documents_ready'.
+    """
+    # 1. Verify case exists and status is appropriate
+    case_raw = await cases_tools.case_get(case_number)
+    case_data = json.loads(case_raw)
+    if "error" in case_data:
+        raise HTTPException(404, f"תיק {case_number} לא נמצא")
+
+    status = case_data.get("status", "")
+    allowed = {"new", "documents_ready"}
+    if status not in allowed:
+        raise HTTPException(
+            409,
+            f"לא ניתן להתחיל תהליך — סטטוס נוכחי: {status}. נדרש: {', '.join(allowed)}",
+        )
+
+    # 2. Create workflow issue in Paperclip
+    try:
+        issue = await pc_create_workflow_issue(case_number, case_data.get("title", ""))
+    except ValueError as e:
+        raise HTTPException(404, str(e))
+    except Exception as e:
+        raise HTTPException(502, f"שגיאת Paperclip: {e}")
+
+    # 3. Wake the CEO agent
+    try:
+        wakeup = await pc_wake_ceo(issue["issue_id"], case_number)
+    except Exception as e:
+        logger.warning("CEO wakeup failed for case %s: %s", case_number, e)
+        wakeup = {"error": str(e)}
+
+    # 4. Update case status to processing
+    await cases_tools.case_update(case_number, status="processing")
+
+    return {
+        "case_number": case_number,
+        "status": "processing",
+        "issue_id": issue["issue_id"],
+        "issue_identifier": issue["identifier"],
+        "project_url": issue["project_url"],
+        "wakeup": wakeup,
+    }
+
+
 # ── Settings: Tag → Company Mappings ──────────────────────────────
 
 @app.get("/api/settings/paperclip-companies")
diff --git a/web/paperclip_client.py b/web/paperclip_client.py
index cead8fa..85d44a8 100644
--- a/web/paperclip_client.py
+++ b/web/paperclip_client.py
@@ -12,6 +12,7 @@ import os
 import uuid
 
 import asyncpg
+import httpx
 
 logger = logging.getLogger(__name__)
 
@@ -20,6 +21,9 @@ PAPERCLIP_DB_URL = os.environ.get(
 )
 
 PLUGIN_ID = "53461b5a-7f58-411a-9952-72f9c8d4a328"  # marcusgroup.legal-ai
+CEO_AGENT_ID = "752cebdd-6748-4a04-aacd-c7ab0294ef33"
+PAPERCLIP_API_URL = os.environ.get("PAPERCLIP_API_URL", "http://localhost:3100")
+PAPERCLIP_BOARD_API_KEY = os.environ.get("PAPERCLIP_BOARD_API_KEY", "")
 
 # Company IDs from Paperclip DB
 COMPANIES = {
@@ -251,3 +255,80 @@ async def get_project_url(case_number: str) -> str | None:
         return None
     finally:
         await conn.close()
+
+
+async def create_workflow_issue(case_number: str, title: str) -> dict:
+    """Create a workflow issue in the existing Paperclip project for a case.
+
+    Returns dict with issue_id, identifier, project_url.
+    Raises ValueError if no project found.
+    """
+    conn = await asyncpg.connect(PAPERCLIP_DB_URL)
+    try:
+        # Find existing project
+        row = await conn.fetchrow(
+            "SELECT id, company_id FROM projects WHERE name LIKE $1",
+            f"%{case_number}%",
+        )
+        if not row:
+            raise ValueError(f"No Paperclip project found for case {case_number}")
+
+        project_id = str(row["id"])
+        company_id = str(row["company_id"])
+
+        # Get company prefix
+        comp_row = await conn.fetchrow(
+            "SELECT issue_prefix FROM companies WHERE id = $1::uuid", company_id,
+        )
+        prefix = comp_row["issue_prefix"] if comp_row and comp_row["issue_prefix"] else "CMP"
+
+        # Create the workflow issue
+        issue_id, identifier = await _create_issue(
+            conn, company_id, project_id, case_number,
+            f"התחל תהליך ניסוח — {title}"[:200], prefix,
+        )
+
+        # Link to legal-ai case via plugin state
+        await _link_case_to_issue(conn, issue_id, case_number)
+
+        project_url = f"https://pc.nautilus.marcusgroup.org/{prefix}/projects/{project_id}/issues"
+        logger.info("Created workflow issue %s for case %s", identifier, case_number)
+
+        return {
+            "issue_id": issue_id,
+            "identifier": identifier,
+            "project_url": project_url,
+        }
+    finally:
+        await conn.close()
+
+
+async def wake_ceo_agent(issue_id: str, case_number: str) -> dict:
+    """Wake the CEO agent via Paperclip's wakeup API.
+
+    MUST use API, never direct DB insert (agent won't wake from DB insert).
+    """
+    if not PAPERCLIP_BOARD_API_KEY:
+        raise RuntimeError("PAPERCLIP_BOARD_API_KEY not set — cannot wake CEO agent")
+
+    url = f"{PAPERCLIP_API_URL}/api/agents/{CEO_AGENT_ID}/wakeup"
+    payload = {
+        "source": "web-ui",
+        "triggerDetail": "user",
+        "reason": f"start_workflow_{case_number}",
+        "payload": {
+            "issueId": issue_id,
+            "mutation": "workflow_start",
+        },
+    }
+
+    async with httpx.AsyncClient(timeout=15) as client:
+        resp = await client.post(
+            url,
+            json=payload,
+            headers={"Authorization": f"Bearer {PAPERCLIP_BOARD_API_KEY}"},
+        )
+        resp.raise_for_status()
+        result = resp.json()
+        logger.info("CEO agent wakeup for case %s: %s", case_number, result)
+        return result