By Harriet Christie, Chief Operating Officer, Mirrorweb
Let’s face it: iMessage isn’t just where we share memes, plan dinner, or chat with friends anymore. It’s also where business gets done—and that’s a big deal in financial services. From quick client updates to team decisions, financial professionals have been using mobile messaging apps like iMessage to communicate for years.
Convenient? Absolutely. But for financial firms, it’s also a recipe for compliance chaos. Regulators don’t care if your conversation happened over email, phone, or iMessage—if it’s business-related, it’s fair game. And failing to capture those communications? That could cost you millions in fines, not to mention your reputation.
So, let’s break this down: Why does iMessage compliance matter, what’s at stake if you ignore it, and how can your firm get ahead of the game?
Why iMessage Deserves Your Attention
iMessage is everywhere. iPhone has led the US smartphone market since 2009 and had a 58.81% market share in 2024. Your employees use it because it’s quick, familiar, and built into their iPhones. Updating a client? Fire off a message. Clarifying a trade with a colleague? Hit send. It’s the fastest way to get things done.
But here’s the catch: regulators aren’t giving you a pass for convenience. All business-related conversations must be monitored and archived. This isn’t optional—it’s the law. Regulations like SEC Rule 17a-4 and FINRA Rule 4511 make sure of that. Yes, even that friendly thread with the client who only sends emojis.
Compliance Matters
What happens if you don’t bother capturing iMessage communications? Spoiler: It’s expensive – and messy.
Fines That Will Keep Your CFO Up at Night
History has made it clear: non-compliance is an expensive misstep. Since 2021, the SEC has fined Wall Street giants over $2 billion for failing to monitor employee messages on unauthorized apps. Think that’s extreme? It’s not. Non-compliance is a direct invitation for regulators to knock on your door—and it won’t be a friendly visit.
Alarming Customers
Trust is the currency of financial services. Clients need to know their money is in the hands of a compliant, reliable, and transparent firm. Being dragged into headlines over a compliance misstep erodes that trust – and rebuilding it takes years.
Operational Nightmares
Regulatory investigations aren’t just expensive; they’re disruptive. Teams get pulled away from strategic priorities to address audits, field legal questions and sift through endless requests for information. It’s quicksand for productivity.
Bottom line? Ignoring iMessage compliance is reckless and unsustainable.
Why Capturing iMessage is Tough
Compliance may be critical, but it’s not simple. Capturing iMessage communications comes with unique challenges:
1. Encryption
iMessage is end-to-end encrypted. While great for user privacy, it creates hurdles for compliance teams. Capturing encrypted content requires sophisticated tools that can bridge the gap without compromising security.
2. BYOD Challenges
Many employees rely on personal devices for work. While that’s great for productivity, monitoring business communications on personal devices raises privacy concerns. How can firms enforce compliance without overstepping boundaries?
3. Outdated Systems
Most legacy systems were designed to capture emails and phone calls, but not modern messaging apps. This tech gap leaves many firms playing catch-up in today’s complex communication world.
The Benefits of Capturing iMessage Communications
Compliance isn’t just about avoiding penalties; it’s an opportunity to gain a competitive advantage. Here’s how:
1. Trust from Regulators
When you capture iMessage messages, you’re not just checking a compliance box— signaling that your firm is proactive, transparent, and head of the curve. Regulators notice and are more likely to trust firms that prioritize compliance.
2. Better Client Relationships
Clients appreciate flexibility. Using clients’ preferred channels keeps them happy and speeds up the process. This also applies to employees; they are using platforms they are most comfortable using which means greater morale, heightened efficiency, and better results.
3. Spot Trouble Before It Escalates
From insider trading to unauthorized disclosures, compliance monitoring isn’t just about keeping the regulators happy, it’s also about protecting your firm from internal risks. Capturing iMessage lets you catch potential issues early, before they spiral into something worse. Early detection is the key to mitigating risks.
4. Streamlined Operations
Modern archiving tools automate capturing and storing communications, so your team can focus on compliance strategy rather than manual monitoring. It’s a win-win for efficiency and accuracy.
5. Reputation Insurance
When your compliance game is airtight, it shows. Clients and stakeholders notice, and that trust pays dividends in the long run.
Getting Started with iMessage Compliance
Ready to tackle iMessage compliance into a strategic advantage? Here’s how to get started:
1. Upgrade Your Tech
Invest in compliance platforms that capture and archive complex communication channels. Look for compliance tools that handle encryption, integrate seamlessly with existing systems, and automate tedious tasks.
2. Refresh Your Policies
If your compliance policy doesn’t explicitly mention iMessage, it’s time for an update. Ensure employees know what’s allowed, what’s not allowed, and how their communications are being monitored. Clarity is key.
3. Train Your Teams
Compliance isn’t everyone’s favorite topic, but it’s essential. Host training sessions and provide easy-to-follow guides to ensure everyone knows the stakes and their role.
4. Respect Privacy (and Stay Legal)
Monitoring personal devices can be tricky, but achievable with the right approach. Use tools that separate business and personal communications and be transparent about monitoring practices.
The Bottom Line: Compliance Is Non-Negotiable
iMessage isn’t going anywhere, and neither are the regulators. Ignoring the compliance challenges it presents isn’t just a risk; it’s gambling with your firm’s future.
The good news? With the right tools, policies, and mindset, iMessage compliance can become a competitive advantage, streamlining operations, affording flexibility, and building trust with customers and regulators.
Do the Markets Believe Trump? Not Exactly
By Jeff O’Connor, Head of Equity Market Structure, Americas at Liquidnet
Ezra Klein’s recent New York Times op-ed, Don’t Believe Him, lays out a stark warning: Donald Trump’s second administration is poised to follow a deliberate strategy of chaos and media saturation, a playbook borrowed from Steve Bannon’s infamous “flood the zone” approach. It’s a tactic designed to overwhelm, distract, and manipulate public perception. But as we considered Klein’s thesis, we found ourselves asking a different question: What about the markets? Do they believe him?
The executive order illusion
The narrative of rule by “executive fiat” is something that the media sees headline value in—headline-grabbing directives designed to shock and set the tone. But this is hardly a new phenomenon. The past three presidents have aggressively wielded executive orders, and the all-time record-holder remains Franklin D. Roosevelt nearly a century ago.
Yes, some of Trump’s executive orders are designed purely for spectacle. But judicial review acts as a hard stop on the more legally dubious moves—whether it’s Trump’s attempt to end birthright citizenship or Biden’s student loan forgiveness plan. Both were ultimately unconstitutional, yet both succeeded in rallying their respective political bases. The markets, however, aren’t buying the theater.
Tariffs and the market’s selective attention
If there’s one area where Trump’s presidency has made waves in market movements, it’s trade policy. The Constitution grants Congress authority over commerce with foreign nations, but by framing trade disputes as national security concerns, the president has more latitude to act unilaterally. Tariffs have been the most influential factor in day-to-day market swings, but even their power appears to be fading.
Consider the market’s reaction to Trump’s recent announcement of punitive tariffs on Canada, Mexico, and China. Overnight futures plunged, signaling a heavy risk-off day. But by market close, concessions had been made, plans altered, and the damage mitigated. It was less an economic shift than a diplomatic chess move. Fast forward a week, and another round of tariff announcements, this time on aluminum and steel. The market barely blinked.
The predictability of the Trump trade
Despite the theatrics, the 2024 U.S. election cycle was one of the most investable in recent history. The market priced in a Trump victory well in advance, with asset class movements and prediction markets signaling the odds.
The Trump trade is a familiar formula: tariffs fueling inflation, tax cuts driving growth, deficit spending increasing and deregulation benefiting banks. The dollar strengthens (now the second most crowded trade after mega-cap tech), interest rates rise, gold gains and financials outperform. These trades were set in motion early and continue to play out.
But not everything is working as expected. The assumption that small-cap stocks would benefit from deregulation has yet to materialize. The reason? Higher interest rates are stifling borrowing costs, and with 10-year Treasury yields hovering around 4.5%—the highest in 18 years—businesses are struggling to adjust to a new, costlier capital environment.
The real market headwind
The biggest market challenge right now isn’t Trump’s policies. It’s the declining expectation of Federal Reserve rate cuts. Since the Fed’s hawkish December message, volatility has crept in, macro uncertainty is rising, and institutional trading volumes are dented. Cash deployment is high, and equity exposure remains concentrated in a few major players.
Meanwhile, corporate earnings for Q4 have been solid, but expectations for 2025 are even loftier. Every economic data release, particularly inflation measures like CPI and PPI, now carries heightened market scrutiny. With 40% of S&P 500 companies citing currency impacts in their earnings reports, the strength of the dollar is top of mind, and the tariff narrative is particularly poignant across a wide swath of the top U.S. companies.
A market caught between signals
So, do the markets believe Trump? Not exactly. Markets don’t trade on slogans or speeches. They trade on policy and execution. The broader themes—tariffs, tax cuts, deregulation—are priced in, but the sustainability of Trump’s economic strategies remains uncertain. Investors are wary of overexposure, cautious of macroeconomic headwinds, and navigating a market environment filled with both opportunity and risk.
Whether Wall Street believes Trump or not, there are many factors at this stage of the cycle introducing opaqueness and trepidation into the markets. The reality is that uncertainty, not conviction, is the prevailing sentiment.