Upland Software Inc. (UPLD) Options Positioning, Max Pain & Unusual Sweeps

$3.98 +2.05% NASDAQ • Live Quote vs Prior Daily Close (Synced Snapshot) EXT / AFTER-HRS: $3.99

Upland Software Inc. (UPLD) carries a Roarable Rating of D- (Sell) with 39/100 RQD Confidence due to weak cash-flow efficiency and sensitivity to current interest rates. Wait for business cash flow and institutional buying to improve before committing fresh capital.

ROARABLE D- • RED ALERT Cap $11.5M
📤 Share Live RQD Speedometer Card: 𝕏 Post Reddit StockTwits ⬇ Live SVG Card
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🤖 Mara Quenwick • AI Quant Lead (Click for Instant Brief) Is UPLD stock a Buy, Hold, or Sell right now according to Roarable's RQD model?
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As of 2026-11-02, Upland Software Inc. (NASDAQ: UPLD) is rated D- (Sell / SELL) by Roarable's 5-pillar RQD engine with a composite confidence score of 39/100 at a spot price of $3.98 (+2.05% 1D, market cap $11.5M). Pillar breakdown: Fundamental Cash Engine 8/20, Institutional 13F & Options Flow 8/20, Executive Insider Alignment 10/20, FRED Macro Regime Fit 6/20, and SEC Balance-Sheet Forensics 7/20. Across 714 tracked Technology issuers, UPLD ranks #509 in composite RQD confidence.

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🤖 Ellis Vennor • AI Peer & Flow Quant (Click for Instant Brief) How does UPLD compare to GIXI and YAAS in the Technology sector?
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Within the Technology sector (Computer Software: Prepackaged Software), UPLD carries a Roarable D- (39/100 RQD), trailing P/E of N/A, gross margin of 74.8%, and ROIC of 2.4%. By comparison, GIXI (Gix Internet Ltd.) holds a D grade (46/100 RQD, P/E N/A, ROIC —, cap $10.5M) and YAAS (Youxin Technology Ltd (Class A)) posts a D- grade (36/100 RQD, P/E N/A, ROIC —, cap $12.7M). Among the 5-stock peer group, UPLD leads on earnings multiple (N/A) while UPLD leads on capital efficiency (2.4% ROIC).

✓ Pre-computed one-to-many AI Quant brief
🤖 Gideon Ashmere • AI SEC 10-K Forensics (Click for Instant Brief) What are the biggest fundamental strengths and SEC risk factors for UPLD?
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Per UPLD's SEC EDGAR XBRL 10-K filing (FY2025, filed 2025-12-31, CIK 0001505155), Upland Software Inc. generated $216.9M in revenue (-21.1% YoY), $40.4M in net income, and $24.4M in free cash flow against $413.2M in total assets and $224.7M in total debt. Key quantitative strengths: Established market leader in Technology with deep daily trading liquidity.. Primary risk factors monitored: Company executives have done more routine share selling than personal cash buying lately.. Institutional options positioning shows a 50% call / 50% put premium split.

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INTERACTIVE SCENARIO DECK:
🛡️ Portfolio Crash X-Ray
EXT / AFTER-HRS: $3.99 (+0.18%)🧬 Disciplined Float (+0.16% YoY Shares)⚙️ Cash Engine: 8/20 (D-) • 11.3% FCF Margin
Verify 90D Bucket Audit →
📊 Historical Track Record Warning: Scores below 50 (39/100 · D-) historically underperformed SPY in 71% of rolling 90-day windows (-7.6% avg 90D alpha vs SPY • 29.0% hit rate).
Audit Bucket Track Record →
RQD QUANT TACHOMETERRED ALERT • D-
025507510039
3-of-3 JEV AI Jury Bearish Warning
Cash
SEC
Whale

Impersonal quantitative research (0–100 RQD rubric) — not individualized investment advice. Past performance does not guarantee future results. Full Disclaimer

5-PILLAR SNOWFLAKE RADARRw D- · Rk D-
Cash (8)Whales (8)SEC (10)Macro (6)CEO (7)
Each axis scored 0–20
12M PRICE TARGET CONE-8.5% Base Target
$23 Bull$4 Base$3 Bear
📬 FREE UPLD RATING-CHANGE & BRIEFING ALERTSManage / Unsubscribe
WHALE OPTIONS SNAPSHOT: — (No Active Options Snapshot on file for UPLD)Realized 20D OHLCV Swing Band: ±12.5%
Deterministic 5-Pillar Attribution (39/100 Composite)
🔍 WHY UPLD SCORES 39/100 (D-) — TOP 3 DRIVERS2 Bullish Pillars + #1 Risk Drag
▲ #1 Bullish Driver: SEC 10-K Forensic Risk+10/20 pts (26% of score)

Altman Z-Score 0.20 (DISTRESS RISK (<1.8)) • Piotroski F-Score 4/9

▲ #2 Bullish Driver: Cash Engine Quality+8/20 pts (21% of score)

SEC XBRL FY 2025 (10-K): 11.3% FCF Margin ($24.4M FCF) & 74.8% Gross Margin

▼ #1 Drag / Risk Factor: Macro Regime Fit6/20 pts (-14 pt drag)

Macro rate sensitivity & RSI-14 (56.5) create a -14 pt regime headwind

📈 PAST 4 QUARTERS RQD vs SUBSEQUENT RETURNQ1 → Q2 → Q3 → Current
Q1 (-3Q)
31
Grade E$3.24+2.5% Next Q
Q2 (-2Q)
34
Grade E$3.32+18.7% Next Q
Q3 (-1Q)
36
Grade E$3.94+1% Next Q
Current
39
Grade D-$3.98-7.6% Hist 90D α
Trajectory: E (31) → D- (39)Full Audit →
⚔️ ADVERSARIAL OPPOSING CASE & FORENSIC KILL-SWITCH (WHY THE BULL/BEAR THESIS COULD FAIL)CONTRARIAN TURNAROUND & SHORT-SQUEEZE DOSSIER

⚔️ Adversarial Opposing Case: What Could Spark a UPLD Turnaround Squeeze

Gideon Ashmere Forensic Desk →

While UPLD currently carries a cautious 39/100 (D-) rating due to Macro Regime Fit (6/20), shorts face asymmetric squeeze risk if free cash flow inflects or management executes accretive buybacks.

🚀 Contrarian Squeeze Trigger #1

Established market leader in Technology with deep daily trading liquidity.

🚀 Contrarian Squeeze Trigger #2

Options & Short-Covering Gamma: Reclaiming the 50-day SMA ($3.71) and Max Pain ($4.18) forces dealer call-delta covering toward $22.57.

🚀 Contrarian Squeeze Trigger #3

Forensic Repair Trigger: Halting share dilution (Disciplined Float (+0.16% YoY Shares)) or retiring high-cost debt immediately upgrades the SEC 10-K Forensic pillar.

🎲 LIVE PREDICTION MARKET ODDS TIED TO $UPLD• $4.8M Crowd Pool • Kalshi / Polymarket Composite
Contract: “UPLD Beats Next Quarterly Revenue & EPS Consensus + Hyperscaler AI CapEx Holds Record Pace”
CALL VS. PUT WHALE SHARE
— (No Active Options Snapshot)
Put/Call Ratio: — (No Active Options Snapshot)
MAX-PAIN EXPIRATION MAGNET
— (No Active Options Snapshot)
No active options chain max-pain snapshot on file
HISTORICAL 20D VOLATILITY SWING
±12.5%
Derived from 20D OHLCV bars (No Active Options Snapshot)

Active Strike Call vs. Put Concentration Ladder (UPLD)

— (No Active Options Snapshot) — No unusual CBOE strike concentration anomalies recorded in the current database snapshot for UPLD.

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Red-Light Warning Desk: Spotting SEC Cash-Flow & Dilution Risks Before Downgrades (Featuring UPLD)

  • ✓Walkthrough of UPLD's RQD Radar, SEC cash-conversion gap & downside invalidation levels
  • ✓3 asymmetric Bear/Hedge frameworks when 10-year Treasury yields stay elevated
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RQD INSIDER CLUB WAITLIST$49/YR PLANNED
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UPLD // CANDLESTICK & AUTO-TRENDLINE WORKSTATION6M: -44.72%⚡ TESTING RESISTANCE
2026-11-02O $3.91H $3.98L $3.90C $3.98VOL 36.4K
RES: $4.02SUP: $2.57SMA50: $3.71SMA200: $6.40
$17.08$13.19$9.31$5.43$1.54RES $4.02SUP $2.57$3.982026-05-042026-06-172026-08-042026-09-172026-11-02
PRIMARY-SOURCE FORENSICS, SECOND-ORDER LINKS & AI ANALYST DESK

UPLD Dilution Monitor, Expectations Hurdle, Butterfly Connections & Policy Exposure

Share Count & Dilution Monitor (#25)

Multi-year comparable XBRL diluted share count not disclosed (ETF or recent listing).

Reverse-DCF Expectations Hurdle (#30)
34.3%/yr Implied 5Y Growth

vs. -21.1% actual YoY revenue growth (assuming 9.25% cost of equity & 16.5x terminal multiple).

Ellis Vennor Setup Ledger (#33)

No active Ellis Vennor swing setup published on UPLD today. View full Setup Ledger →

🦋 Documented & Second-Order Butterfly Connections Open Graph →

No direct multi-tier Butterfly edges indexed yet for UPLD. Explore sector supply chains on /butterfly.

AI Analyst Theses, Washington Policy & Company Video
🎬 No recent verified company-specific video clip queued for UPLD today (we never pad ticker pages with unrelated generic clips). Browse Macro Video Desk →
DETERMINISTIC MULTI-FACTOR EQUITY AUDIT • SEC EDGAR XBRL × RQD PEER BENCHMARK

📊 Quantitative Sector Peer Comparison, SEC Filing Delta & Investment FAQ (UPLD)

Technology Rank #509 of 714 ⚔️ GIXI vs UPLD Full Matrix →

1. Head-to-Head Technology Peer Comparison (UPLD vs. GIXI, YAAS, SMSI, ALAR)

Industry: Computer Software: Prepackaged Software (222 Tracked Issuers)

Across 714 tracked Technology securities in the Roarable RQD universe, Upland Software Inc. (UPLD) ranks #509 by composite RQD confidence (39/100, grade D-) and #639 by equity capitalization ($11.5M). Within this direct 5-issuer industry benchmark cohort, UPLD leads on earnings valuation at N/A trailing P/E, while UPLD leads on capital efficiency and profitability with 2.4% ROIC and 74.8% gross margin. GIXI currently holds the highest overall quantitative score in the immediate peer group at 46/100 (D) compared with UPLD at 39/100 (D-).

Ticker / Company Roarable Grade RQD Score Trailing P/E Gross Margin ROIC 1D Change Market Cap Head-to-Head
UPLD ACTIVE
Upland Software Inc.
D- 39/100 — 74.8% 2.4% +2.05% $11.5M Benchmark Subject
GIXI
Gix Internet Ltd.
D 46/100 — — — -7.56% $10.5M /gixi-vs-upld →
YAAS
Youxin Technology Ltd (Class A)
D- 36/100 — 33.4% — -5.60% $12.7M /yaas-vs-upld →
SMSI
Smith Micro Software Inc.
E 28/100 — 74.1% -35.0% -3.40% $13.1M /smsi-vs-upld →
ALAR
Alarum Technologies Ltd.
D 45/100 — — — -4.41% $9.9M /alar-vs-upld →

2. Multi-Year SEC XBRL Revenue, Cash Flow & Balance-Sheet Trajectory (FY2023–FY2025)

SEC EDGAR 10-K • FILED 2025-12-31 • CIK 0001505155

In its most recent audited fiscal period (FY2025, filed 2025-12-31), Upland Software Inc. (UPLD) reported GAAP revenue of $216.9M (-21.1% vs. FY2024 revenue of $274.8M , and -27.2% cumulative change since FY2023) , GAAP net income of $40.4M, operating cash flow of $25.8M, and free cash flow of $24.4M (+4.7% YoY). On the balance sheet, UPLD closed FY2025 with $413.2M in total assets against $224.7M in total debt (Altman Z-Score: 0.20, Piotroski F-Score: 4/9).

Fiscal Period Filing Date Revenue Net Income Operating Cash Flow Free Cash Flow Total Assets Total Debt
FY2025 (FY) 2025-12-31 $216.9M $40.4M $25.8M $24.4M $413.2M $224.7M
FY2024 (FY) 2024-12-31 $274.8M $112.7M $24.2M $23.4M $529.5M $287.0M
FY2023 (FY) 2023-12-31 $297.9M $179.9M $49.9M $49.9M — —

3. UPLD Data-Verified Investor FAQ (RQD Rating, Sector Peers, SEC Forensics & Technicals)

✓ SCHEMA.ORG FAQPAGE JSON-LD ENABLED

Is UPLD stock a Buy, Hold, or Sell right now according to Roarable's RQD model?

As of 2026-11-02, Upland Software Inc. (NASDAQ: UPLD) is rated D- (Sell / SELL) by Roarable's 5-pillar RQD engine with a composite confidence score of 39/100 at a spot price of $3.98 (+2.05% 1D, market cap $11.5M). Pillar breakdown: Fundamental Cash Engine 8/20, Institutional 13F & Options Flow 8/20, Executive Insider Alignment 10/20, FRED Macro Regime Fit 6/20, and SEC Balance-Sheet Forensics 7/20. Across 714 tracked Technology issuers, UPLD ranks #509 in composite RQD confidence.

How does UPLD compare to GIXI and YAAS in the Technology sector?

Within the Technology sector (Computer Software: Prepackaged Software), UPLD carries a Roarable D- (39/100 RQD), trailing P/E of N/A, gross margin of 74.8%, and ROIC of 2.4%. By comparison, GIXI (Gix Internet Ltd.) holds a D grade (46/100 RQD, P/E N/A, ROIC —, cap $10.5M) and YAAS (Youxin Technology Ltd (Class A)) posts a D- grade (36/100 RQD, P/E N/A, ROIC —, cap $12.7M). Among the 5-stock peer group, UPLD leads on earnings multiple (N/A) while UPLD leads on capital efficiency (2.4% ROIC).

What are the biggest fundamental strengths and SEC risk factors for UPLD?

Per UPLD's SEC EDGAR XBRL 10-K filing (FY2025, filed 2025-12-31, CIK 0001505155), Upland Software Inc. generated $216.9M in revenue (-21.1% YoY), $40.4M in net income, and $24.4M in free cash flow against $413.2M in total assets and $224.7M in total debt. Key quantitative strengths: Established market leader in Technology with deep daily trading liquidity.. Primary risk factors monitored: Company executives have done more routine share selling than personal cash buying lately.. Institutional options positioning shows a 50% call / 50% put premium split.

Where is UPLD trading relative to its 50-day, 200-day, and 52-week technical levels?

UPLD last traded at $3.98 (+2.05% on volume of 47,368 shares), positioning the stock +7.28% above its 50-day simple moving average ($3.71) and -37.81% below its 200-day simple moving average ($6.40). Across its 52-week range of $2.75 to $21.50, UPLD sits at the 6.6% percentile with a 14-day RSI of 56.5 (BULLISH MOMENTUM) and an implied next-earnings move of ±12.5% ($3.48 to $4.48).

UPLD Investor FAQ & Complete 8-Part Research Index

100% OPEN ACCESS • SEC EDGAR × CBOE × FRED

What is UPLD's options positioning and volatility profile?

Roarable tracks verified CBOE unusual options sweeps, put/call ratios, and OHLCV realized volatility bands for UPLD.

ROARABLE RATING BRIEF • RQD 39/100 (D-) ✓ STAGE-C NUMBER FIREWALL VERIFIED

UPLD — Upland Software Inc.: What the Facts Mean to a Prospective Investor

Engine: anthropic/claude-haiku-5.5
As of: 2026-11-02T15:51:26Z

Roarable Rating Brief: What This Means to a Prospective Investor

The Roarable RQD rating is 39 out of 100, a letter grade of D-, with the verdict "Roarable Sell — Vulnerable Balance Sheet & Flow," per the Roarable RQD rating. Across its five pillars:

  • Fundamental Cash Engine: 8 / 20. The pillar reflects ROIC of 2.4% and FCF yield of 0%, per the Roarable RQD rating and Market Data. Low returns on invested capital and no free-cash-flow yield at the current market value point to a weak cash-generation profile relative to the capital base.
  • Whale / 13F Flow: 8 / 20. The pillar label references institutional accumulation and options positioning. No 13F holder detail is provided in the source data, so the underlying drivers of this score cannot be verified here.
  • Insider Conviction: 7 / 20. The pillar label references SEC Form 4 and Congressional PTR cluster flow. No insider or Congressional transaction detail is provided in the source data.
  • Macro Regime Fit: 6 / 20. The pillar reflects Beta of 1.0 and sector sensitivity, per the Roarable RQD rating and Market Data. A beta of 1.0 means the stock is stated to move in line with the broad market; the score penalizes the stock's sector sensitivity.
  • Forensic Balance Sheet: 10 / 20. The pillar cites Altman Z of 0.2, Piotroski F of 4/9, and Debt/Equity of 0.5, per the Roarable RQD rating. An Altman Z near zero and a mid-range Piotroski score indicate balance-sheet and financial-health stress; the Debt/Equity figure is a moderating factor but does not offset the other two.

For a prospective investor evaluating the stock today, the rating points to a weak cash engine and a stressed balance sheet as the dominant concerns, with flow signals also scoring weakly. Potential upside drivers in the source data are limited to the recent positive earnings-related news wire item (see Recent Catalysts). Valuation tradeoffs are visible in the Market Data: EV/EBITDA of 37.1 sits against a market cap of $11.5M and an operating margin of 2%, which means the enterprise-value multiple is high relative to reported operating profitability. The rating is descriptive of the source data and is not personalized financial advice.

Business

Upland Software Inc. (UPLD) is a NASDAQ-listed issuer in the Technology sector, Computer Software: Prepackaged Software industry, per the Profile. The source data does not describe its specific products, customer base, or revenue model. Revenue figures are available in the SEC financials, but their composition is not described.

Financial Trend

PeriodRevenueOperating IncomeNet IncomeEPSFCFCashDebt
FY 2025$216.9M$4.4M$40.4MN/A$24.4M$29.4M$224.7M
FY 2024$274.8M$-102.3M$112.7MN/A$23.4M$56.4M$287.0M
FY 2023$297.9M$-163.9M$179.9MN/A$49.9MN/AN/A

Per the SEC financials, revenue declined from $297.9M (FY 2023) to $274.8M (FY 2024) to $216.9M (FY 2025). Operating income was negative in FY 2023 and FY 2024 and positive at $4.4M in FY 2025, while reported net income ($40.4M in FY 2025) exceeded operating income in each period shown. Per the Market Data, the operating margin is 2%, the net margin is 18.6%, and the gross margin is 74.8%; ROIC is 2.4%. The source data reports an Altman Z-Score of 0.2 and a Piotroski F-Score of 4/9 (per the Roarable RQD rating), and FY 2025 debt of $224.7M against cash of $29.4M.

Recent Catalysts & News Wire Analysis

Per the Recent News & Catalysts section, the feed contains six items, all tagged to UPLD and sourced from aggregators and market-data sites:

  • Catalyst (green light): A report of an earnings beat for UPLD's Q2 2026 results, described as an EPS beat of 15.46% against estimate, with shares edging higher. This is the only item flagged as a catalyst.
  • Market wire (yellow light): Several items reference options-chain quotes, financial ratios, estimates, and a Simply Wall St note describing softer revenue offset by margin resilience.
  • Market wire (yellow light): A report of a 8.2% rally to $3.96 with buyers pushing toward resistance.

Risk watch items drawn from the feed: the Simply Wall St headline cites softer revenue; the revenue trend in the SEC financials is also declining. The Butterfly Supply-Chain Graph reports no proprietary signals (see below).

Open Questions

  • What drives the revenue decline from $297.9M (FY 2023) to $216.9M (FY 2025), and what is the revenue composition by product or customer?
  • What explains the gap between negative operating income and substantially positive reported net income in FY 2023 and FY 2024?
  • What are the debt maturity schedule and covenant terms behind $224.7M of FY 2025 debt against $29.4M of cash?
  • What is the basis for the reported Q2 2026 EPS beat, and what EPS figures underlie it, given that EPS is shown as N/A in the financials?
  • Who are the institutional and insider holders, and what are their recent transactions?

UPLD Live News Feed, Press Releases & Catalyst Wire

Real-time company headlines, analyst actions, and sector developments for Upland Software Inc. (UPLD) • Click "Debate This Headline" to argue it in the Roar Pit below

💬 Jump to UPLD Debate Forum (3) ↓
🔥 THE ROAR PIT • LIVE COMMUNITY DEBATE 3 Active Posts & Replies

UPLD Bull vs. Bear Conversation Board — What's Your Call at $3.98?

🐂 33% BULLISH CONVICTION COMMUNITY TUG-OF-WAR ON UPLD 🐻 67% BEARISH CONVICTION
1. Pick Your Side on UPLD:
💡 Tip: Back up your call with a price target or RQD metric to get upvoted to the top.
RO RoarDesk_Moderator Roarable Research Desk 🐻 BEARISH 🎯 Target: $3.43 (-12.1%)
📌 Pinned Debate

🔥 Official Bull vs. Bear Debate: Is UPLD (D- • RQD 39/100) a Buy at $3.90?

Welcome to the UPLD (Upland Software Inc.) Roar Pit. Current RQD Composite is 39/100 (Roarable Sell — Vulnerable Balance Sheet & Flow) in Computer Software: Prepackaged Software. Bulls point to operating leverage and sector positioning, while bears focus on macro rate sensitivity and margin execution. Pick your side (🐂 Bull or 🐻 Bear) and drop your price target below.

MU MultipleCompression Forensic Accounting Watch 🐻 BEARISH 🎯 Target: $2.96 (-24.1%)
Spot @ $3.90

Pump the brakes on UPLD — check the valuation vs. margin headwinds

Everyone in here is repeating the bull case on UPLD, but look at what you are paying: current EV/EBITDA multiples with 74.8% gross margins. Unless Upland Software Inc. expands free cash flow yield next quarter, I would rather wait for a pullback closer to the 200-day moving average before touching this.

MI MidwestValue Verified K Arena Trader 🐂 BULLISH 🎯 Target: $4.76 (+22.1%)
Spot @ $3.90

UPLD cash flow & RQD setup is being underpriced by the Street here

Looking at the 5-pillar RQD breakdown on UPLD, the market is fixating on short-term headline noise in Computer Software: Prepackaged Software and ignoring the balance sheet and cash flow trajectory. At $3.90 (52-wk range $2.75 - $21.50), any beat on forward guidance forces shorts and underweight funds to chase.

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