diff --git a/web/src/tabs/PositionsTab.dom.test.tsx b/web/src/tabs/PositionsTab.dom.test.tsx
index bcdeba7..d2641dc 100644
--- a/web/src/tabs/PositionsTab.dom.test.tsx
+++ b/web/src/tabs/PositionsTab.dom.test.tsx
@@ -350,6 +350,45 @@ describe('PositionsTab DOM behavior', () => {
         });
     });
 
+    it('exposes a manage-in-plans action for eligible live bot holdings', async () => {
+        const now = Date.now();
+        fetchPositionsBootstrapMock.mockResolvedValue({
+            entries: [],
+            orders: [{
+                id: 'entry-order',
+                order_id: 'entry-order',
+                profile_id: 'p1',
+                symbol: 'BTC/USDT',
+                type: 'Market',
+                side: 'BUY',
+                qty: 1,
+                price: 100,
+                status: 'filled',
+                timestamp: now - 1_000,
+                created_at: new Date(now - 1_000).toISOString(),
+                trade_id: 'TRD-POS-1',
+                action: 'ENTRY',
+                source: 'BOT'
+            }],
+            historyTradeKeys: [],
+            profiles: [{ id: 'p1', name: 'High Risk Scalper' }]
+        });
+
+        const onManageHolding = vi.fn();
+        const user = userEvent.setup();
+        render(<PositionsTab botState={buildBotState(now)} onManageHolding={onManageHolding} />);
+
+        await user.click(await screen.findByRole('button', { name: 'High Risk Scalper' }));
+        const manageButtons = await screen.findAllByRole('button', { name: 'Manage in Plans' });
+        await user.click(manageButtons[0]);
+
+        expect(onManageHolding).toHaveBeenCalledWith(expect.objectContaining({
+            symbol: 'BTC/USDT',
+            profileId: 'p1',
+            tradeId: 'TRD-POS-1'
+        }));
+    });
+
     it('handles non-admin bootstrap failures with empty-state fallback', async () => {
         authState.user = { id: 'user-2' };
         authState.profile = { role: 'trader' };
diff --git a/web/src/tabs/PositionsTab.tsx b/web/src/tabs/PositionsTab.tsx
index 3c728ae..2cb153b 100644
--- a/web/src/tabs/PositionsTab.tsx
+++ b/web/src/tabs/PositionsTab.tsx
@@ -8,9 +8,10 @@ import { Layers, ListFilter, Link2, GitBranch, AlertTriangle, Lock, RefreshCw, C
 import { useCanonicalLifecycle } from '../hooks/useCanonicalLifecycle';
 import { fetchPositionsBootstrap } from '../lib/positionsApi';
 
-interface PositionsTabProps {
-    botState: BotState;
-}
+interface PositionsTabProps {
+    botState: BotState;
+    onManageHolding?: (position: HybridPosition) => void;
+}
 
 interface HybridPosition {
     source: 'BOT' | 'MANUAL';
@@ -414,7 +415,7 @@ export const assignLifecycleTradeIds = (
     return enriched;
 };
 
-export const PositionsTab = ({ botState }: PositionsTabProps) => {
+export const PositionsTab = ({ botState, onManageHolding }: PositionsTabProps) => {
     const { user, profile } = useAuth();
     const [manualPositions, setManualPositions] = useState<HybridPosition[]>([]);
     const [simplePlanMetaByTradeId, setSimplePlanMetaByTradeId] = useState<Record<string, { holdingMode: 'short_term' | 'long_term'; automationState?: string | null }>>({});
@@ -1433,41 +1434,51 @@ export const PositionsTab = ({ botState }: PositionsTabProps) => {
                                                 <div className="text-xs font-mono text-gray-500">-</div>
                                             )}
                                         </td>
-                                        <td className="px-6 py-4 text-right">
-                                            {pos.source === 'BOT' && (
-                                                <button
-                                                    onClick={async () => {
-                                                        if (!confirm(`Are you sure you want to CLOSE ${pos.symbol}?`)) return;
-                                                        try {
-                                                            const accessToken = await getPlatformAccessToken();
-                                                            const response = await fetch(`${tradingRuntime.tradingApiUrl}/api/close`, {
-                                                                method: 'POST',
-                                                                headers: {
-                                                                    'Content-Type': 'application/json',
-                                                                    'Authorization': `Bearer ${accessToken}`,
-                                                                    'x-request-id': createRequestId('web-close')
-                                                                },
-                                                                body: JSON.stringify({
-                                                                    profile_id: pos.profileId,
-                                                                    symbol: pos.symbol
-                                                                })
-                                                            });
-                                                            const data = await response.json();
-                                                            if (data.success) {
-                                                                alert(`Successfully closed ${pos.symbol}`);
-                                                            } else {
-                                                                alert(`Failed to close: ${data.error}`);
-                                                            }
-                                                        } catch (e: any) {
-                                                            alert(`Error: ${e.message}`);
-                                                        }
-                                                    }}
-                                                    className="px-2 py-1 bg-red-500/10 hover:bg-red-500/20 text-red-400 border border-red-500/20 rounded text-[10px] font-bold uppercase transition-colors"
-                                                >
-                                                    Square Off
-                                                </button>
-                                            )}
-                                        </td>
+                                        <td className="px-6 py-4 text-right">
+                                            <div className="flex items-center justify-end gap-2">
+                                                {pos.source === 'BOT' && pos.profileId && pos.tradeId && onManageHolding && (
+                                                    <button
+                                                        onClick={() => onManageHolding(pos)}
+                                                        className="px-2 py-1 bg-sky-500/10 hover:bg-sky-500/20 text-sky-300 border border-sky-500/20 rounded text-[10px] font-bold uppercase transition-colors"
+                                                    >
+                                                        Manage in Plans
+                                                    </button>
+                                                )}
+                                                {pos.source === 'BOT' && (
+                                                    <button
+                                                        onClick={async () => {
+                                                            if (!confirm(`Are you sure you want to CLOSE ${pos.symbol}?`)) return;
+                                                            try {
+                                                                const accessToken = await getPlatformAccessToken();
+                                                                const response = await fetch(`${tradingRuntime.tradingApiUrl}/api/close`, {
+                                                                    method: 'POST',
+                                                                    headers: {
+                                                                        'Content-Type': 'application/json',
+                                                                        'Authorization': `Bearer ${accessToken}`,
+                                                                        'x-request-id': createRequestId('web-close')
+                                                                    },
+                                                                    body: JSON.stringify({
+                                                                        profile_id: pos.profileId,
+                                                                        symbol: pos.symbol
+                                                                    })
+                                                                });
+                                                                const data = await response.json();
+                                                                if (data.success) {
+                                                                    alert(`Successfully closed ${pos.symbol}`);
+                                                                } else {
+                                                                    alert(`Failed to close: ${data.error}`);
+                                                                }
+                                                            } catch (e: any) {
+                                                                alert(`Error: ${e.message}`);
+                                                            }
+                                                        }}
+                                                        className="px-2 py-1 bg-red-500/10 hover:bg-red-500/20 text-red-400 border border-red-500/20 rounded text-[10px] font-bold uppercase transition-colors"
+                                                    >
+                                                        Square Off
+                                                    </button>
+                                                )}
+                                            </div>
+                                        </td>
                                     </tr>
                                 )})
                             ) : (
diff --git a/web/src/views/PortfolioView.tsx b/web/src/views/PortfolioView.tsx
index f79b18f..6672e19 100644
--- a/web/src/views/PortfolioView.tsx
+++ b/web/src/views/PortfolioView.tsx
@@ -1,4 +1,5 @@
 import { useState } from 'react';
+import { useNavigate } from 'react-router-dom';
 import { useAppContext } from '../context/AppContext';
 import { PositionsTab } from '../tabs/PositionsTab';
 import { HistoryTab } from '../tabs/HistoryTab';
@@ -9,6 +10,7 @@ type Tab = typeof TABS[number];
 
 export function PortfolioView() {
   const { botState } = useAppContext();
+  const navigate = useNavigate();
   const [tab, setTab] = useState<Tab>('Positions & Orders');
 
   return (
@@ -31,7 +33,19 @@ export function PortfolioView() {
         ))}
       </div>
 
-      {tab === 'Positions & Orders' && <PositionsTab botState={botState} />}
+      {tab === 'Positions & Orders' && (
+        <PositionsTab
+          botState={botState}
+          onManageHolding={(position) => {
+            const params = new URLSearchParams({
+              mode: 'sell',
+              symbol: position.symbol,
+            });
+            if (position.tradeId) params.set('tradeId', position.tradeId);
+            navigate(`/simple?${params.toString()}`);
+          }}
+        />
+      )}
       {tab === 'Trade History'      && <HistoryTab botState={botState} />}
     </div>
   );
diff --git a/web/src/views/SimpleView.test.ts b/web/src/views/SimpleView.test.ts
index fcf15fb..a92df99 100644
--- a/web/src/views/SimpleView.test.ts
+++ b/web/src/views/SimpleView.test.ts
@@ -205,6 +205,6 @@ describe('SimpleView helpers', () => {
         profitValue: '6',
         notes: '',
       },
-    })).toThrow('Sell setups require an existing Simple holding for this symbol.');
+    })).toThrow('Sell setups require an existing holding for this symbol.');
   });
 });
diff --git a/web/src/views/SimpleView.tsx b/web/src/views/SimpleView.tsx
index b26f651..1f84e56 100644
--- a/web/src/views/SimpleView.tsx
+++ b/web/src/views/SimpleView.tsx
@@ -1,6 +1,7 @@
 import { useEffect, useMemo, useRef, useState } from 'react';
 import type { FormEvent } from 'react';
 import { Pencil, RefreshCw, Trash2 } from 'lucide-react';
+import { useSearchParams } from 'react-router-dom';
 import { useAppContext } from '../context/AppContext';
 import { fetchChartBars, fetchResearchProfile } from '../lib/marketApi';
 import {
@@ -201,7 +202,7 @@ export function buildSimpleSetupPayload(input: {
   const automationState = normalizeAutomationState(existingEntry?.automation_state, existingEntry || { status: side === 'buy' ? 'simple_armed_buy' : 'simple_armed_sell' } as ManualEntryPayload);
 
   if (side === 'sell' && !holding) {
-    throw new Error('Sell setups require an existing Simple holding for this symbol.');
+    throw new Error('Sell setups require an existing holding for this symbol.');
   }
 
   if (side === 'buy' && parseNonNegativeNumber(input.draft.dropValue) === null) {
@@ -280,7 +281,7 @@ function buildPreviewText(draft: SimpleSetupDraft, holding: SimpleHolding | null
   }
 
   if (!holding) {
-    return `Sell ${symbol} only works when a Simple holding already exists.`;
+    return `Sell ${symbol} only works when an eligible existing holding is available.`;
   }
 
   const profitTargetPrice = computeProfitTargetPrice(holding.entryPrice, draft.profitMode, draft.profitValue);
@@ -616,6 +617,7 @@ function describeSavedSetup(entry: ManualEntryPayload): string {
 
 export function SimpleView() {
   const { botState } = useAppContext();
+  const [searchParams, setSearchParams] = useSearchParams();
   const [profiles, setProfiles] = useState<TradeProfilePayload[]>([]);
   const [savedSetups, setSavedSetups] = useState<ManualEntryPayload[]>([]);
   const [editingSetupId, setEditingSetupId] = useState<string | null>(null);
@@ -626,7 +628,9 @@ export function SimpleView() {
   const [copiedKey, setCopiedKey] = useState<string | null>(null);
   const [message, setMessage] = useState<string | null>(null);
   const [error, setError] = useState<string | null>(null);
+  const [selectedHoldingTradeId, setSelectedHoldingTradeId] = useState<string | null>(null);
   const marketPriceRequestSymbolRef = useRef<string>('');
+  const consumedPrefillRef = useRef(false);
 
   const normalizedSymbol = draft.symbol.trim().toUpperCase();
   const symbolState = botState?.symbols && typeof botState.symbols === 'object' ? botState.symbols : {};
@@ -651,6 +655,24 @@ export function SimpleView() {
       .filter((position) => position.symbol && position.size > 0 && position.entryPrice > 0);
   }, [botState?.positions, simpleAutoProfile?.id]);
 
+  const availableSellHoldings = useMemo(() => {
+    const positions = normalizeRuntimeArray<typeof botState.positions[number]>(botState?.positions);
+    return positions
+      .map((position) => ({
+        symbol: String(position.symbol || '').trim().toUpperCase(),
+        size: Number(position.size || 0),
+        entryPrice: Number(position.entryPrice || 0),
+        profileId: position.profileId,
+        tradeId: position.tradeId,
+      }))
+      .filter((position) => position.symbol && position.size > 0 && position.entryPrice > 0 && position.profileId && position.tradeId)
+      .sort((left, right) => {
+        const bySymbol = left.symbol.localeCompare(right.symbol);
+        if (bySymbol !== 0) return bySymbol;
+        return String(left.tradeId || '').localeCompare(String(right.tradeId || ''));
+      });
+  }, [botState?.positions]);
+
   const runtimeOrders = useMemo(() => {
     const orders = normalizeRuntimeArray<Record<string, any>>(botState?.orders);
     return orders.filter((order) => {
@@ -663,21 +685,19 @@ export function SimpleView() {
     [botState?.operationalEvents],
   );
 
-  const matchingHolding = useMemo(
-    () => simpleHoldings.find((holding) => holding.symbol === normalizedSymbol) || null,
-    [simpleHoldings, normalizedSymbol],
-  );
-  const availableSellHoldings = useMemo(
-    () => [...simpleHoldings].sort((left, right) => left.symbol.localeCompare(right.symbol)),
-    [simpleHoldings],
-  );
+  const selectedSellHolding = useMemo(() => {
+    if (selectedHoldingTradeId) {
+      return availableSellHoldings.find((holding) => holding.tradeId === selectedHoldingTradeId) || null;
+    }
+    return availableSellHoldings.find((holding) => holding.symbol === normalizedSymbol) || null;
+  }, [availableSellHoldings, normalizedSymbol, selectedHoldingTradeId]);
 
   const supportedSymbols = useMemo(() => {
     const fromState = Object.keys(symbolState || {}).map(normalizeKnownSymbol).filter(Boolean) as string[];
     const fromSetups = savedSetups.map((entry) => normalizeKnownSymbol(entry.symbol)).filter(Boolean) as string[];
-    const fromHoldings = simpleHoldings.map((holding) => normalizeKnownSymbol(holding.symbol)).filter(Boolean) as string[];
+    const fromHoldings = availableSellHoldings.map((holding) => normalizeKnownSymbol(holding.symbol)).filter(Boolean) as string[];
     return Array.from(new Set([...fromState, ...fromSetups, ...fromHoldings, ...COMMON_SIMPLE_SYMBOLS])).sort((left, right) => left.localeCompare(right));
-  }, [symbolState, savedSetups, simpleHoldings]);
+  }, [symbolState, savedSetups, availableSellHoldings]);
 
   const filteredSymbolSuggestions = useMemo(() => {
     if (!normalizedSymbol) {
@@ -747,16 +767,23 @@ export function SimpleView() {
   }, [normalizedSymbol, livePrice, draft.currentMarketPrice, loadingPrice, supportedSymbols]);
 
   const previewText = useMemo(
-    () => buildPreviewText(draft, draft.side === 'sell' ? matchingHolding : null),
-    [draft, matchingHolding],
+    () => buildPreviewText(draft, draft.side === 'sell' ? selectedSellHolding : null),
+    [draft, selectedSellHolding],
   );
 
   function updateDraft<K extends keyof SimpleSetupDraft>(key: K, value: SimpleSetupDraft[K]) {
+    if (key === 'side' && value === 'buy') {
+      setSelectedHoldingTradeId(null);
+    }
+    if (key === 'symbol' && draft.side === 'sell') {
+      setSelectedHoldingTradeId(null);
+    }
     setDraft((prev) => ({ ...prev, [key]: value }));
   }
 
   function applyHoldingToDraft(holding: SimpleHolding) {
     setMarketPriceSource(null);
+    setSelectedHoldingTradeId(holding.tradeId || null);
     setDraft((prev) => ({
       ...prev,
       side: 'sell',
@@ -768,10 +795,35 @@ export function SimpleView() {
 
   useEffect(() => {
     if (draft.side !== 'sell') return;
-    if (matchingHolding) return;
+    if (selectedSellHolding) return;
     if (availableSellHoldings.length === 0) return;
     applyHoldingToDraft(availableSellHoldings[0]);
-  }, [draft.side, matchingHolding, availableSellHoldings]);
+  }, [draft.side, selectedSellHolding, availableSellHoldings]);
+
+  useEffect(() => {
+    if (consumedPrefillRef.current) return;
+    const requestedMode = String(searchParams.get('mode') || '').trim().toLowerCase();
+    const requestedSymbol = String(searchParams.get('symbol') || '').trim().toUpperCase();
+    const requestedTradeId = String(searchParams.get('tradeId') || '').trim();
+    if (requestedMode !== 'sell') return;
+    if (availableSellHoldings.length === 0) return;
+
+    const selected = (requestedTradeId
+      ? availableSellHoldings.find((holding) => holding.tradeId === requestedTradeId)
+      : null)
+      || (requestedSymbol
+        ? availableSellHoldings.find((holding) => holding.symbol === requestedSymbol)
+        : null)
+      || availableSellHoldings[0];
+
+    if (selected) {
+      applyHoldingToDraft(selected);
+      setMessage(`Loaded ${selected.symbol} from Portfolio. Configure the profit target and save the plan.`);
+      setError(null);
+    }
+    consumedPrefillRef.current = true;
+    setSearchParams({}, { replace: true });
+  }, [availableSellHoldings, searchParams, setSearchParams]);
 
   async function copyIdentifier(kind: 'trade' | 'order', value: string | null | undefined) {
     if (!value) return;
@@ -867,7 +919,7 @@ export function SimpleView() {
       const payload = buildSimpleSetupPayload({
         draft,
         existingId: editingSetupId || undefined,
-        holding: draft.side === 'sell' ? matchingHolding : null,
+        holding: draft.side === 'sell' ? selectedSellHolding : null,
         existingEntry,
       });
 
@@ -958,7 +1010,7 @@ export function SimpleView() {
   }
 
   const saveButtonLabel = editingSetupId ? 'Update setup' : 'Save setup';
-  const saveButtonDisabled = submitting || loadingPrice || (draft.side === 'sell' && !matchingHolding);
+  const saveButtonDisabled = submitting || loadingPrice || (draft.side === 'sell' && !selectedSellHolding);
 
   return (
     <div className="space-y-8">
@@ -978,6 +1030,7 @@ export function SimpleView() {
               type="button"
               onClick={() => {
                 setEditingSetupId(null);
+                setSelectedHoldingTradeId(null);
                 setMarketPriceSource(draft.currentMarketPrice ? marketPriceSource : null);
                 setDraft({
                   ...DEFAULT_DRAFT,
@@ -1002,6 +1055,7 @@ export function SimpleView() {
                 onClick={() => {
                   setError(null);
                   setMessage(null);
+                  setSelectedHoldingTradeId(null);
                   setDraft((prev) => ({ ...prev, side: 'buy' }));
                 }}
                 className={`rounded-[1.25rem] border px-4 py-4 text-left transition ${
@@ -1041,9 +1095,9 @@ export function SimpleView() {
               <label className="space-y-2">
                 <span className="text-[11px] font-black uppercase tracking-[0.24em] text-zinc-700">Existing holding</span>
                 <Select
-                  value={matchingHolding?.symbol || normalizedSymbol}
+                  value={selectedHoldingTradeId || ''}
                   onChange={(e) => {
-                    const selected = availableSellHoldings.find((holding) => holding.symbol === e.target.value);
+                    const selected = availableSellHoldings.find((holding) => (holding.tradeId || '') === e.target.value);
                     if (selected) applyHoldingToDraft(selected);
                   }}
                   disabled={availableSellHoldings.length === 0}
@@ -1052,7 +1106,7 @@ export function SimpleView() {
                     <option value="">No eligible holdings available</option>
                   ) : (
                     availableSellHoldings.map((holding) => (
-                      <option key={`${holding.symbol}:${holding.tradeId || 'holding'}`} value={holding.symbol}>
+                      <option key={`${holding.symbol}:${holding.tradeId || 'holding'}`} value={holding.tradeId || ''}>
                         {holding.symbol} · {holding.size} @ {holding.entryPrice.toFixed(4)}
                       </option>
                     ))
@@ -1215,9 +1269,9 @@ export function SimpleView() {
                     Holding size
                   </span>
                   <Input
-                    value={draft.side === 'sell' && matchingHolding ? String(matchingHolding.size) : draft.quantity}
+                    value={draft.side === 'sell' && selectedSellHolding ? String(selectedSellHolding.size) : draft.quantity}
                     onChange={(e) => updateDraft('quantity', e.target.value)}
-                    readOnly={draft.side === 'sell' && !!matchingHolding}
+                    readOnly={draft.side === 'sell' && !!selectedSellHolding}
                     className="read-only:bg-[var(--muted)]"
                     placeholder="10"
                   />
@@ -1284,13 +1338,13 @@ export function SimpleView() {
 
             {draft.side === 'sell' && (
               <div className={`rounded-[1.5rem] border px-4 py-4 text-sm ${
-                matchingHolding
+                selectedSellHolding
                   ? 'border-emerald-500/20 bg-emerald-500/10 text-emerald-700 dark:text-emerald-300'
                   : 'border-red-500/20 bg-red-500/10 text-red-700 dark:text-red-300'
               }`}>
-                {matchingHolding
-                  ? `Simple holding ready: ${matchingHolding.symbol} · ${matchingHolding.size} units at ${matchingHolding.entryPrice.toFixed(4)}. Executed Simple buys also appear in Portfolio as live positions.`
-                  : 'No existing Simple holding found for this symbol. Sell setups only arm against a current Simple holding.'}
+                {selectedSellHolding
+                  ? `Holding ready: ${selectedSellHolding.symbol} · ${selectedSellHolding.size} units at ${selectedSellHolding.entryPrice.toFixed(4)}. Executed buys also appear in Portfolio as live positions.`
+                  : 'No eligible live holding found for this symbol yet. Managed sell setups only arm against a current holding.'}
               </div>
             )}