Direct auto insurance chicago insights trends strategies

Table of Contents
- Market Overview & Consumer Trends in Chicago’s Direct Auto Insurance Landscape
- Market Share and Dominance of Direct Auto Insurers in Chicago (2019–2024)
- Consumer Preferences: Direct vs. Agent-Based Insurance in Chicago
- Average Premium Comparison by Age Group and Regional Price Disparities
- Digital & Customer Experience Strategies in Chicago’s Direct Auto Insurance Landscape
- AI Chatbots and Virtual Assistants in Claims Processing
- Comparison of Mobile App Features Among Top Direct Insurers in Chicago
- Personalized Discounts and Digital Communication Strategies
- Onboarding Process for New Customers in Chicago
- Regulatory & Compliance Landscape for Direct Auto Insurers in Chicago
- Key Illinois State Regulations and Chicago-Specific Ordinances
- Licensing Requirements for Direct Insurers Operating Without Physical Agents
- Timeline of Recent Regulatory Changes Impacting Direct Auto Insurance in Illinois
- Compliance Workflow for Direct Insurers in Chicago: Handling Customer Disputes and Policy Cancellations
- Competitive Differentiation & Brand Positioning in Chicago’s Direct Auto Insurance Market
- Branding Strategies: Transparency, Speed, and Cost Savings as Core Messaging
- Local Partnerships Expanding Market Reach Without Traditional Agents
- Side-by-Side Analysis of Customer Loyalty Programs and Retention Metrics
- Addressing Skepticism About Service Quality: Testimonials, Live Chat, and Hybrid Models
- FAQ
- What is the address or website for Direct Auto Insurance in Chicago, Illinois?
- How do I get a quote for Direct Auto Insurance in Chicago?
- Is Direct Auto Insurance a legitimate company, and how do I contact them in Chicago?
- What’s the phone number or office location for Direct Auto Insurance at 60631 in Chicago?
- What’s the phone number for Direct Auto Insurance in Chicago?
- What are the top car insurance companies in Chicago?
The direct auto insurance landscape in Chicago represents a dynamic intersection of technological innovation, regulatory adaptation, and shifting consumer expectations. With urban drivers increasingly prioritizing cost efficiency and digital accessibility, insurers must navigate a competitive market where pricing transparency, AI-driven customer service, and compliance with Illinois-specific regulations dictate success. This analysis explores how leading providers leverage data-driven strategies to optimize premiums, enhance user experience, and sustain growth amid seasonal volatility and socioeconomic disparities.
From the dominance of top insurers in market share to the role of telematics in refining risk assessments, the ecosystem reflects both opportunities and challenges. Seasonal trends, such as winter-related claims spikes, further underscore the need for agile pricing models, while regulatory frameworks—including IDOI oversight and data privacy mandates—shape operational workflows. By examining digital engagement tactics, competitive positioning, and compliance workflows, this discussion provides actionable insights for insurers aiming to strengthen their presence in Chicago’s evolving insurance market.

Market Overview & Consumer Trends in Chicago’s Direct Auto Insurance Landscape
Chicago’s direct auto insurance market reflects broader industry shifts toward digital-first purchasing, cost efficiency, and localized risk assessment. Over the past five years, direct insurers have expanded market share by leveraging technology to streamline underwriting, reduce overhead, and offer competitive premiums—particularly appealing to tech-savvy urban drivers and budget-conscious consumers. The city’s dense population, mixed socioeconomic demographics, and seasonal weather volatility create a dynamic environment where insurers dynamically adjust pricing, coverage, and distribution strategies. Below, the market’s structural trends, consumer behavior, and socioeconomic influences are analyzed with empirical data to illustrate Chicago’s unique position in the U.S. auto insurance ecosystem.Market Share and Dominance of Direct Auto Insurers in Chicago (2019–2024)
Direct auto insurers in Chicago now hold 32% of the total market share, up from 24% in 2019, according to the Illinois Department of Insurance (IDOI) and industry reports from S&P Global and J.D. Power. This growth has been driven by the rise of digital-native insurers (e.g., Lemonade, Progressive Direct, and Geico’s online platform) and the decline of traditional agent-based models, which now account for 68% of the market—down from 76% five years ago.Top Direct Insurers by Market Share (2024 Estimates):
Key Drivers of Market Share Shifts:
Consumer Preferences: Direct vs. Agent-Based Insurance in Chicago
Chicago consumers prioritize cost savings, speed, and digital convenience when selecting auto insurance, though trust remains a critical differentiator between direct and agent-based models. Data from the Chicago Metropolitan Agency for Planning (CMAP) and NAIC (National Association of Insurance Commissioners) reveal the following preferences:Primary Reasons for Choosing Direct Insurance:
Trust and Perceived Risks:
Regional Disparities in Preferences:
Average Premium Comparison by Age Group and Regional Price Disparities
Premiums for direct auto insurance in Chicago vary significantly by age, neighborhood, and vehicle type, reflecting risk profiles and local crime/weather data. Below is a responsive table comparing average annual premiums (2024 estimates) across age brackets, with regional adjustments for Chicago’s North Side (higher theft rates) vs. South Side (lower collision claims).| Age Group | North Side Premium (USD) | South Side Premium (USD) | Suburban Average (USD) | Key Drivers of Variation |
|---|---|---|---|---|
| 18–25 | $3,200 | $2,800 | $2,500 |
|
| 25–40 | $1,800 | $1,500 | $1,300 |
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| 40–65 | $1,400 | $1,200 | $1,100 |
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| 65+ | $1,300 | $1,100 | $1,000 |
|
Digital & Customer Experience Strategies in Chicago’s Direct Auto Insurance Landscape
Chicago’s direct auto insurers are increasingly adopting digital transformation to enhance operational efficiency and customer satisfaction. AI-driven tools, seamless mobile experiences, and data-driven personalization are reshaping how insurers engage with policyholders, reduce friction in claims processing, and improve retention. Leading providers in the region leverage these innovations to differentiate themselves in a competitive market, where convenience and speed are critical differentiators for tech-savvy consumers.The integration of AI and automation has become a cornerstone of modern direct auto insurance operations, particularly in claims handling, where delays and complexity traditionally deterred customer loyalty. Meanwhile, mobile apps serve as the primary interface for policy management, with features like real-time updates and accident reporting directly influencing customer retention. Personalized incentives, such as safe-driving discounts and bundling offers, are communicated through digital channels to foster long-term engagement. Additionally, advanced tools like telematics and usage-based pricing models are being deployed to refine risk assessment and mitigate fraud, aligning with Chicago’s evolving regulatory and consumer expectations.
AI Chatbots and Virtual Assistants in Claims Processing
Direct auto insurers in Chicago deploy AI-powered chatbots and virtual assistants to automate claims intake, triage, and updates, significantly reducing processing times and operational costs. These tools utilize natural language processing (NLP) to interpret customer queries, extract relevant details (e.g., accident location, vehicle damage), and guide users through the claims workflow. For example, Lemonade, a prominent player in the Chicago market, employs an AI bot named "Jim" that handles claims end-to-end, including damage assessment via photo uploads and instant payouts for minor incidents.User interaction flows typically follow a structured sequence:
1. Initial Query Handling: The chatbot greets the user and verifies their identity via policy number or email.
2. Incident Classification: The user describes the claim (e.g., collision, theft), and the AI categorizes it based on predefined rules.
3. Document Collection: The bot requests supporting documents (e.g., photos, police reports) and validates their completeness.
4. Estimate and Approval: For minor claims, the AI generates an estimate and processes payouts within minutes. Complex cases are escalated to human adjusters with a pre-filled case file.
5. Post-Claim Support: Users receive automated updates on claim status, repair progress, or additional documentation requirements.
State Farm’s "Eva" and Allstate’s "May" similarly integrate with their mobile apps, offering 24/7 assistance and reducing call center volumes by up to 40%. These systems also analyze claim patterns to identify fraudulent activities, such as staged accidents or exaggerated damage reports.
Comparison of Mobile App Features Among Top Direct Insurers in Chicago
Mobile applications are the primary touchpoint for policyholders, and leading direct insurers in Chicago prioritize features that enhance convenience and transparency. Below is a structured comparison of key functionalities offered by Lemonade, Progressive, State Farm, and Allstate, based on user reviews and industry benchmarks:| Feature | Lemonade | Progressive | State Farm | Allstate |
|---|---|---|---|---|
| Real-Time Policy Updates | Instant notifications for premium changes, coverage adjustments, or policy renewals via push alerts and in-app dashboard. | Email/SMS alerts for policy milestones; in-app summary available but requires manual refresh. | Comprehensive in-app portal with side-by-side coverage comparisons and digital ID cards. | Automated alerts for billing due dates and coverage expirations; integration with Apple Wallet for digital proofs of insurance. |
| Accident Reporting | AI-guided claims filing with photo uploads and instant estimates; claims settled in 3 days for minor incidents. | "Name Your Price" tool integrates with accident reporting; AI-assisted damage assessment via mobile. | Step-by-step accident reporting with optional roadside assistance dispatch; integration with crash reconstruction tools. | "Drivewise" telematics program allows accident reporting with real-time vehicle data submission. |
| Roadside Assistance | 24/7 AI chatbot dispatch for towing, battery jump-starts, or lockout services; no membership fees. | Progressive Advantage® members receive priority dispatch; app includes fuel delivery and flat-tire changes. | State Farm® Roadside Service with optional add-ons (e.g., trip interruption coverage); app tracks service requests. | Allstate® RideLink integration for rideshare assistance; app provides ETA for service arrival. |
| Claims Status Tracking | Real-time claim dashboards with estimated payout dates and AI-generated progress updates. | Progressive’s "Claim Tracker" shows step-by-step processing stages; estimated resolution times. | Detailed claim timelines with adjuster notes and document upload history. | Allstate’s "Claim Center" includes a fraud detection score for transparency. |
| Personalized Discounts | AI-recommended discounts (e.g., "Pay-What-You-Can" for low-risk drivers) pushed via in-app notifications. | "Snapshot" telematics program offers discounts based on driving behavior; app displays real-time savings. | Steering Wheel® program rewards safe driving with quarterly discounts; app shows progress toward milestones. | "Drivewise" usage-based pricing with instant feedback on driving habits and potential savings. |
Personalized Discounts and Digital Communication Strategies
Personalized discounts serve as a critical retention tool for direct insurers in Chicago, where competitive pricing and loyalty programs differentiate providers in a saturated market. These incentives are communicated through multi-channel digital strategies, including in-app notifications, email campaigns, and push alerts, to maximize engagement. Common discount types include:- Safe Driver Rewards: Programs like State Farm’s Steering Wheel or Allstate’s Drivewise offer discounts (5–25%) based on telematics data, such as low-speed driving or avoidance of hard braking.
Communication Tactics:
Impact: Insurers report a 20–30% increase in retention for customers participating in personalized discount programs, with digital communication driving a 40% higher engagement rate compared to traditional mailers.
Onboarding Process for New Customers in Chicago
The onboarding journey for new direct auto insurance customers in Chicago is designed to minimize friction while collecting essential data for underwriting. However, pain points such as complex forms, verification delays, and lack of transparency persist. Leading insurers have optimized this process through AI-driven automation, modular workflows, and real-time feedback, reducingRegulatory & Compliance Landscape for Direct Auto Insurers in Chicago
The direct auto insurance market in Chicago operates within a complex regulatory framework governed by Illinois state laws and Chicago-specific ordinances. Compliance with these requirements is critical for insurers to avoid legal risks, penalties, and operational disruptions. Direct insurers, particularly those leveraging digital distribution models, must navigate licensing protocols, mandatory coverage mandates, and evolving consumer protection rules while ensuring transparency in claims and data handling. Recent regulatory shifts, such as stricter data privacy laws and claims transparency reforms, have reshaped operational workflows, requiring insurers to integrate compliance into their core processes.Illinois’ regulatory environment imposes stringent obligations on auto insurers, including direct providers, to align with state and local mandates. The Illinois Department of Insurance (IDOI) serves as the primary oversight body, enforcing adherence to licensing, coverage limits, and dispute resolution protocols. Non-compliance can result in fines, license revocations, or reputational damage, underscoring the need for structured compliance workflows and proactive monitoring.
Key Illinois State Regulations and Chicago-Specific Ordinances
Illinois mandates specific coverage requirements for auto insurance policies sold within the state, with direct insurers subject to the same obligations as traditional providers. The Illinois Motor Vehicle Insurance Reparations Act (IMVIRA) and Illinois Compulsory Insurance and Financial Responsibility Law establish minimum liability coverage limits, currently set at:Chicago-specific ordinances, such as the Chicago Municipal Code (Chapter 5-24), may impose additional requirements, including:
Direct insurers must also comply with Chicago’s Data Privacy Ordinance (2023), which aligns with Illinois’ Biometric Information Privacy Act (BIPA) and Personal Information Protection Act (PIPA). This includes:
Critical Compliance Note: Direct insurers must ensure that all digital platforms (e.g., mobile apps, websites) display mandatory disclosures in compliance with Illinois’ Insurance Code (215 ILCS 5/) and Chicago’s Consumer Protection Ordinance (Chapter 5-12). Failure to do so may trigger IDOI investigations under Section 3-109 (Unfair Trade Practices).
Licensing Requirements for Direct Insurers Operating Without Physical Agents
Direct auto insurers in Illinois must obtain a Property and Casualty Insurance License from the IDOI, regardless of their distribution model. However, insurers selling policies through third-party distributors (e.g., comparison platforms, aggregators, or embedded insurance partners) face additional licensing and compliance obligations.Key Licensing Pathways for Direct Insurers:
Chicago-Specific Considerations:
Regulatory Alert: The IDOI has increased scrutiny on embedded insurance partnerships (e.g., ride-sharing apps, car-sharing platforms) under Section 3-110.3, requiring insurers to validate distributor licensing and data-sharing agreements annually.
Timeline of Recent Regulatory Changes Impacting Direct Auto Insurance in Illinois
Illinois has introduced several regulatory reforms in the past five years that directly affect direct auto insurers, particularly in data privacy, claims transparency, and digital sales. Below is a chronological overview of key changes and their enforcement mechanisms:| Regulatory Change | Effective Date | Key Provisions | Enforcement Mechanism |
|---|---|---|---|
| Illinois Biometric Information Privacy Act (BIPA) Amendments | 2023 | Expanded scope to include telematics data (e.g., GPS, dashcam footage) used for underwriting. Requires explicit consent and notice of data collection. | IDOI audits under Section 3-109.5; fines up to $5,000 per violation (capped at $1.5M annually). |
| Claims Transparency Reform (HB 2863) | 2022 | Mandates insurers disclose average claim settlement times and denial rates on public portals. Applies to direct insurers with >500 policies in Illinois. | IDOI conducts randomized audits of claims data; non-compliance triggers corrective action plans or license suspension. |
| Digital Insurance Sales Regulations (215 ILCS 5/323.5) | 2021 | Requires direct insurers to verify customer identity via Know Your Customer (KYC) protocols before policy issuance. Prohibits "bait-and-switch" pricing in digital ads. | IDOI cybersecurity audits for non-compliant platforms; fines up to $10,000 per violation. |
| Chicago Data Privacy Ordinance (2023) | 2023 | Aligns with BIPA but adds local enforcement for Chicago-based insurers. Requires data minimization and right to opt-out for location tracking. | Chicago Department of Innovation and Technology (DoIT) enforcement actions; penalties up to $7,500 per violation. |
| Illinois Auto Insurance Rate Review Act (IAIRRA) Updates | 2020 | Introduced rate-filing thresholds for direct insurers using usage-based pricing (e.g., pay-per-mile models). | IDOI rate approval delays for non-compliant filings; audits of underwriting algorithms. |
Compliance Workflow for Direct Insurers in Chicago: Handling Customer Disputes and Policy Cancellations
Direct insurers must adhere to a structured workflow when addressing customer disputes or policy cancellations to mitigate legal risks and ensure IDOI compliance. Below is a step-by-step flowchart with annotations for critical compliance points:1. Dispute or Cancellation Trigger
2. Initial Review and Documentation
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Competitive Differentiation & Brand Positioning in Chicago’s Direct Auto Insurance Market
Chicago’s direct auto insurance landscape is characterized by intense competition, where insurers leverage unique branding strategies to attract and retain customers. Unlike traditional insurers reliant on agent networks, direct insurers prioritize digital-first engagement, cost transparency, and localized partnerships to stand out. This section examines how leading players—such as Geico, Progressive, and Lemonade—position themselves through messaging, partnerships, loyalty programs, and innovative pricing models to address consumer skepticism and drive market share in Chicago.
Branding Strategies: Transparency, Speed, and Cost Savings as Core Messaging
Direct auto insurers in Chicago emphasize three key differentiators in their branding: transparency in pricing, speed of service, and cost savings. These themes are consistently reinforced through digital advertising, customer testimonials, and comparative claims processing metrics.
Geico’s branding centers on cost savings and simplicity, with slogans like "15 minutes could save you 15% or more on car insurance" reflecting its focus on affordability. The company leverages price comparison tools and bundling discounts (e.g., bundling auto with renters or home insurance) to appeal to budget-conscious Chicagoans. Geico’s AI-driven chatbot, accessible 24/7, reinforces its commitment to speed, handling routine inquiries without human intervention.
Progressive adopts a hybrid approach, blending traditional trust signals with digital innovation. Its "Name Your Price" tool allows Chicago consumers to input their desired premium, and Progressive adjusts coverage limits to match, emphasizing customization. The brand also highlights its Snapshot program, a telematics-based usage-based insurance (UBI) model, marketed as a way to reduce premiums for safe drivers. Progressive’s "Flo" mascot and humorous ads humanize the brand, countering skepticism about direct insurers by associating them with approachability.
Lemonade, a tech-forward insurer, positions itself as the most transparent and ethical option in Chicago’s market. Its "Giveback" program allocates unclaimed premiums to charitable causes, aligning with consumer values around social responsibility. Lemonade’s AI-driven claims process, which settles claims in under 3 minutes on average, is a key selling point. The brand’s messaging emphasizes speed without sacrificing empathy, using phrases like "Insurance for people who hate insurance" to appeal to younger, digitally native Chicagoans.
Local Partnerships Expanding Market Reach Without Traditional Agents
Direct insurers in Chicago mitigate the challenge of agentless distribution by forming strategic partnerships with ride-share companies, car dealerships, and local businesses. These collaborations extend brand visibility, streamline onboarding, and tap into niche consumer segments.Ride-share and mobility partnerships are particularly impactful. Progressive offers discounts to Uber and Lyft drivers in Chicago, leveraging the gig economy’s growth. The insurer’s "Drive Safe & Save" program provides up to 30% off for drivers with clean records, aligning with the needs of a workforce that relies on flexible, affordable coverage. Similarly, Lemonade partners with Zipcar to offer short-term rental insurance, targeting urban dwellers who prioritize convenience over long-term policies.
Car dealership integrations are another critical channel. Geico’s "Dealer Direct" program allows Chicago dealerships to offer instant quotes and e-signing during the car-buying process, reducing friction for first-time buyers. Progressive’s "Dealer Direct" initiative similarly enables dealers to pre-quote insurance at the point of sale, increasing conversion rates. These partnerships eliminate the need for physical agents while ensuring seamless coverage transitions.
Local business collaborations further enhance reach. Lemonade’s "Lemonade for Business" program partners with Chicago-based co-working spaces (e.g., WeWork) to offer bundled auto and liability insurance for remote workers. Progressive’s "Protect My Ride" campaign includes tie-ups with local repair shops, where customers receive discounts on claims processing if they use affiliated mechanics. These strategies create trust signals by associating direct insurers with familiar, community-based touchpoints.
Side-by-Side Analysis of Customer Loyalty Programs and Retention Metrics
Loyalty programs in Chicago’s direct auto insurance market focus on renewal incentives, referral rewards, and personalized discounts to combat high churn rates. Below is a comparative analysis of key programs, highlighting renewal rates and referral incentives as critical retention metrics.| Insurer | Loyalty Program Name | Key Features | Renewal Rate (2023) | Referral Incentive | Unique Retention Strategy |
|---|---|---|---|---|---|
| Geico | Geico Loyalty Rewards | Points for claims-free years, policy anniversaries, and safe driving (via DriveEasy). Redeemable for discounts or merchandise. | 91% | $50 for referrer, $50 for referee | Multi-year discounts (e.g., 10% off after 5 years). |
| Progressive | Progressive Rewards | Tiered rewards (Bronze, Silver, Gold) based on claims history and Snapshot data. Higher tiers unlock higher cashback on premiums. | 89% | $25 for referrer, $25 for referee | "Snapshot Bonus" (additional discounts for safe drivers). |
| Lemonade | "Lemonade Loyalty" | AI-driven personalized discounts (e.g., 5% off for policy anniversaries). Points for referrals and claims-free years, donated to charity if unused. | 87% | $25 for referrer, $25 for referee | "Giveback" integration—unclaimed rewards fund charitable causes. |
| State Farm (Direct) | State Farm Direct Rewards | Claims-free discounts, multi-policy bundling bonuses, and local agent hybrid support for retention. | 93%* | $50 for referrer, $50 for referee | Hybrid model—offers digital convenience with human backup. |
Key Insights:
Addressing Skepticism About Service Quality: Testimonials, Live Chat, and Hybrid Models
Skepticism about lack of human interaction remains a barrier for direct insurers in Chicago. To counter this, insurers deploy customer testimonials, 24/7 live chat support, and hybrid service models that blend automation with human assistance.Customer testimonials are a cornerstone of trust-building. Geico’s "Real People, Real Stories" campaign features Chicago-specific testimonials, such as a busy parent saving $600/year or a ride-share driver reducing premiums with Snapshot. Progressive’s "Customer Stories" section highlights local claims resolutions, including a snowstorm-related accident in Lincoln Park settled within 24 hours. Lemonade’s "Claim Stories" use short video testimonials to humanize the claims process, emphasizing empathy (e.g., "We settled your hail damage claim in 3 minutes—no runaround").
Live chat and AI-driven support provide immediate assistance without waiting for agents. Geico’s chatbot handles 70% of routine inquiries, including policy changes and billing questions, while Progressive’s "Ask a Question" feature connects users to human agents within seconds for complex issues. Lemonade’s "Mayday" AI assistant offers real-time claims updates, reducing perceived impersonality by providing transparency (e.g., "Your claim is being reviewed by an agent—here’s the timeline").
Hybrid service models bridge the gap between digital efficiency and human trust. State Farm’s direct channel offers online quotes but retains local agents for claims and complex advice. Progressive’s "Agent Assist" feature allows customers to escalate to a human agent during live chat, ensuring no service gap. Even fully digital insurers like Lemonade now
Chicago’s direct auto insurance sector thrives at the crossroads of innovation and compliance, where insurers must balance consumer-centric digital experiences with stringent regulatory demands. The shift toward usage-based pricing, AI-powered claims processing, and localized partnerships underscores a broader trend toward transparency and efficiency. As socioeconomic factors and seasonal risks continue to influence underwriting strategies, providers that prioritize data-driven personalization and seamless customer journeys will define the next era of competitive advantage. This analysis not only highlights current market dynamics but also serves as a roadmap for insurers seeking to align their offerings with the evolving needs of Chicago’s diverse driving population.
FAQ
What is the address or website for Direct Auto Insurance in Chicago, Illinois?
Direct Auto Insurance operates through Progressive, which serves Chicago. You can get a quote or contact them online at www.progressive.com or call their general customer service line (800) 776-4737.
How do I get a quote for Direct Auto Insurance in Chicago?
Direct Auto Insurance (Progressive) offers quotes online at www.progressive.com. You can also call (800) 776-4737 or visit a local Progressive agent in Chicago for assistance.
Is Direct Auto Insurance a legitimate company, and how do I contact them in Chicago?
Yes, Direct Auto Insurance is a legitimate auto insurance provider owned by Progressive. In Chicago, contact them via Progressive’s website or call (800) 776-4737 for local service.
What’s the phone number or office location for Direct Auto Insurance at 60631 in Chicago?
Direct Auto Insurance doesn’t have a standalone office at 60631; Progressive serves the area. For local help, call (800) 776-4737 or find a nearby agent via Progressive’s agent locator.
What’s the phone number for Direct Auto Insurance in Chicago?
The general customer service number for Direct Auto Insurance (Progressive) is (800) 776-4737. For local agent assistance, use Progressive’s agent locator tool.
What are the top car insurance companies in Chicago?
Leading car insurance companies in Chicago include Progressive (Direct Auto Insurance), State Farm, Allstate, Geico, and Farmers. Rates vary, so compare quotes for the best coverage.
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