LIVE
DBX
Dropbox, Inc. · Technology
$29.94
+10.52% this month
VERSUS
⟷
COMPARE
MSFT
Microsoft Corporation · Technology
$390.99
+0.06% this month
Scoreboard verdict
Across AI score, momentum, valuation, upside, operating margin
DBX
2
MSFT
2
Comparison scoreboard
MIXED SETUPAI Score
DBX 30.9
MSFT ✓58.8
1Y Return
DBX ✓+10.52%
MSFT -22.32%
Fwd P/E
DBX ✓8.79
MSFT 19.89
Target Up.
DBX -12.60%
MSFT ✓+45.38%
Op. Margin
DBX N/A
MSFT 46.33%
Metrics last refreshed: 7/14/2026
Quick take
DBX vs MSFT: Dropbox vs Microsoft Stock Comparison: AI Score, Valuation, Performance and Upside
Dropbox is a smaller cloud storage platform fighting Microsoft's OneDrive bundling with AI document workflows and strong FCF generation, while Microsoft is the enterprise cloud and AI giant that bundles OneDrive within its dominant Microsoft 365 subscription. Dropbox is the high-quality underdog FCF story; Microsoft is the AI platform compounder.
DBX vs MSFT is a focused cloud storage FCF business competing against Microsoft's bundled platform versus the enterprise AI cloud giant — Dropbox wins if niche document workflow and simplicity retain SMB users; Microsoft wins by compounding AI monetization across its already-installed enterprise base.
Live analysis · updated 7/14/2026
DBX and MSFT are closely matched — they split the tracked metrics evenly. DBX leads on both 1-year return (+10.52%) and forward P/E quality (8.79x vs 19.89x for MSFT), a relatively favorable combination of momentum and valuation. Analyst consensus implies meaningfully more upside for MSFT (+45.38%) than for DBX (-12.60%).
Normalized 1Y performance
DBX
MSFT
Recent returns
DBX
MSFT
Analyst price targets & sentiment
DBX · 6 analysts
Price target range
analyst low$21.00
analyst high$32.00
analyst mean$26.17
current price$29.94
-12.6% upside to analyst mean
MSFT · 54 analysts
STRONG BUYHOLDSTRONG SELL
Strong Buy (1.3/5.0)
Price target range
analyst low$400.00
analyst high$870.00
analyst mean$559.86
current price$390.99
+45.4% upside to analyst mean
Who should consider this stock?
DBX may suit investors who:
- →value Dropbox's strong FCF generation relative to market cap as a shareholder return driver
- →believe Dropbox's simplicity and DocSend AI features retain users despite OneDrive bundling
- →prefer a focused, profitable cloud storage business vs Microsoft's massive enterprise complexity
- →want a lower-valuation cloud software investment with buyback-funded capital return
MSFT may suit investors who:
- →prefer the world's most complete enterprise AI platform across Azure, Copilot, and Microsoft 365
- →value Microsoft's enterprise distribution advantage that makes OneDrive and Teams defaults for most businesses
- →want durable recurring B2B subscription revenue compounding with AI feature adoption
- →are comfortable paying a premium multiple for Microsoft's enterprise AI monetization breadth
Performance & AI score
| Metric | DBX | MSFT |
|---|---|---|
| AI score | 30.9 | 58.8 |
| AI rank | #2240 | #228 |
| Latest close | $29.94 | $390.99 |
| 1M return | +10.52% | +0.06% |
| 6M return | +9.55% | -18.42% |
| 1Y return | +10.52% | -22.32% |
$10,000 invested — hypothetical growth (dividends reinvested)
How much would $10,000 be worth today if invested at the start of each period, with all dividends reinvested?
| Period | DBX | MSFT |
|---|---|---|
| 1Y ago | $11.05K (+10.5%) started 2025-07-14 | $7.77K (-22.3%) started 2025-07-14 |
| 5Y ago | $9.82K (-1.8%) started 2021-07-14 | $14.8K (+48.0%) started 2021-07-14 |
| 10Y ago | $10.51K (+5.1%) started 2018-03-23 | $92.21K (+822.1%) started 2016-07-14 |
Hypothetical — past performance does not guarantee future results.
Valuation & upside potential
| Metric | DBX | MSFT |
|---|---|---|
| Market cap | $6.99B | $2.86T |
| Trailing P/E | 16.36 | 22.94 |
| Forward P/E | 8.79 | 19.89 |
| Price/Sales | 2.77 | 11.87 |
| EV/Revenue | 3.81 | 9.14 |
| Analyst target | $26.17 | $559.86 |
| Target upside | -12.60% | +45.38% |
Growth, profitability & risk
| Metric | DBX | MSFT |
|---|---|---|
| Revenue growth | 0.80% | 18.30% |
| Earnings growth | -5.90% | 23.40% |
| EPS growth | -5.90% | +23.40% |
| FCF margin | +32.32% | +11.63% |
| Operating margin | N/A | 46.33% |
| Profit margin | 18.71% | 39.34% |
| ROIC proxy | N/A | 34.01% |
| Return on equity | N/A | 34.01% |
| Dividend yield | 0.00% | 0.95% |
| Beta | 0.66 | 1.13 |
| Debt/equity | N/A | 30.27 |
| Current ratio | 1.23 | 1.28 |
| Quick ratio | 1.16 | 1.14 |
Drawdown & downside risk
Lower drawdown and smaller single-period drops generally indicate a smoother ride, though they do not guarantee lower future risk.
1Y risk snapshot
DBX max drawdown31.43%
MSFT max drawdown34.91%
DBX max wkly drop11.47%
MSFT max wkly drop14.43%
5Y risk snapshot
DBX max drawdown41.52%
MSFT max drawdown37.15%
DBX max wkly drop28.23%
MSFT max wkly drop14.43%
10Y risk snapshot
DBX max drawdown62.64%
MSFT max drawdown37.15%
DBX max wkly drop28.23%
MSFT max wkly drop16.36%
Performance metrics by period
| Period | Metric | DBX | MSFT |
|---|---|---|---|
| 1Y | Growth | +10.52% | -22.27% |
| CAGR | +10.53% | -22.35% | |
| Sharpe ratio | 0.33 | -0.96 | |
| Max drawdown | 31.43% | 34.91% | |
| Max daily drop | 8.34% | 9.99% | |
| Max wkly drop | 11.47% | 14.43% | |
| 5Y | Growth | -1.84% | +43.07% |
| CAGR | -0.37% | +7.43% | |
| Sharpe ratio | 0.03 | 0.24 | |
| Max drawdown | 41.52% | 37.15% | |
| Max daily drop | 22.93% | 9.99% | |
| Max wkly drop | 28.23% | 14.43% | |
| 10Y | Growth | +5.13% | +716.39% |
| CAGR | +0.60% | +23.37% | |
| Sharpe ratio | 0.10 | 0.75 | |
| Max drawdown | 62.64% | 37.15% | |
| Max daily drop | 22.93% | 14.74% | |
| Max wkly drop | 28.23% | 16.36% |
Business comparison
| Category | DBX | MSFT |
|---|---|---|
| Company | Dropbox, Inc. | Microsoft Corporation |
| Sector | Technology | Technology |
| Industry | N/A | Software - Infrastructure |
| Core business | Cloud storage and collaboration platform with 700M+ registered users. Dropbox is competing against Microsoft OneDrive's bundling in Microsoft 365 by focusing on AI document workflows, DocSend, and cross-platform collaboration for individuals and SMBs who need a simple, reliable file sync experience. | Azure cloud infrastructure, Microsoft 365 (Word, Excel, Teams, OneDrive, Outlook), Copilot AI, GitHub, Xbox, LinkedIn, and enterprise software across CRM (Dynamics), collaboration (Teams), and analytics (Power BI). |
| Investor focus | ARPU growth through AI features, paying user stabilization, FCF generation, and whether Dropbox can retain users against Microsoft's bundling strategy. | Azure AI growth, Copilot adoption and monetization across Microsoft 365, operating margin sustainability, and enterprise platform lock-in. |
DBX strengths
- →Dropbox is one of the most cash-generative SMB SaaS companies relative to market cap — strong FCF-to-revenue conversion
- →Strong brand among individuals and small teams who prefer Dropbox's simplicity over Microsoft's complexity
- →DocSend adds document analytics and AI workflow value that Microsoft OneDrive does not replicate well for sales teams
MSFT strengths
- →Microsoft 365 bundles OneDrive, Teams, and Copilot with a subscription that is already paid by 400M+ enterprise users
- →Azure is the #2 cloud platform globally and growing fastest among top hyperscalers in some periods
- →Copilot AI across Microsoft 365, GitHub, Dynamics, and Bing creates the broadest enterprise AI monetization surface
Risks to watch — DBX
- →Microsoft OneDrive's inclusion in Microsoft 365 subscriptions creates an existential pricing challenge — most business users already have OneDrive as part of their subscription
- →Paying user growth has plateaued — Dropbox must grow ARPU rather than user count
- →Microsoft Copilot integrated with OneDrive adds AI capabilities that Dropbox must match with its own AI features
Risks to watch — MSFT
- →Azure growth must sustain AI momentum to justify premium multiple
- →Copilot adoption has been slower than initial estimates — AI monetization timeline is uncertain
- →Antitrust pressure on Teams bundling in Europe and potential Copilot bundling scrutiny
Frequently asked questions
Free public comparison
Want deeper AI forecasts?
This comparison page is public and free forever. Subscribers can unlock saved watchlists, full AI rankings, detailed forecasts, and interactive analysis tools.
Related comparisons
More comparisons
Browse all 1,000 comparisons →