IPSec VPN Setup with Cisco ASA and UDM Pro

@kashifnadeem86

As an experienced Azure Solutions Architect Expert and DevOps Engineer with a strong background in networking and security, I have the ideal skills to tackle your VPN setup project. I am well-versed in Cisco ASA and UDM Pro, and have a deep understanding of IPSec VPNs, including AES-256 encryption and PSK authentication - all of which are integral components in your desired setup. With my extensive 10-year experience, I have safely established numerous IPSec VPNs ensuring traffic flows seamlessly between 2 networks. Solving your current issue with traffic flow between your networks will be no different. My solid expertise in cloud platforms also means that should you require any other future adjustments or setups to blend into your existing infrastructure, I am more than capable of delivering. Overall, assisting clients in establishing secure, high-performance connections is one of the core strengths of my skill set as evidenced by my various certifications and track record of successful implementations. So look no further, let's collaborate and ensure your VPN setup is robust, reliable, and future-ready to meet the needs of your business!

@farooqtahir2013

As a seasoned professional with over a decade of hands-on experience in network engineering, I bring an extensive range of skills to the table. Throughout my career, I have effectively planned, implemented and managed complex network infrastructures, prioritizing best practices and high security. Notably, I have worked with industry-leading vendors such as Cisco and Ubiquiti - the key players in this project's equation - ensuring a deep understanding of their technologies. Your issue with traffic flow between the two networks after establishing the VPN tunnel highlights a common complication. However, with my expansive knowledge in addressing such hurdles, I can swiftly identify any misconfigurations or inconsistencies that might be obstructing smooth traffic operations. My commitment to 24-hour availability means I will be diligently troubleshooting and resolving this in real-time. To achieve success with your project, your choice needs to be based on expertise, reliability and an unwavering commitment to your satisfaction - all marks that I hit proudly. With me logging into your team, you gain not just technical talents but also a genuinely collaborative partner who values honest communication and pragmatic problem-solving. Let's turn your VPN challenge into a victory together!

@AwaisChaudhry

Hello, I understand your site-to-site IPSec VPN between Cisco ASA and UDM Pro uses AES-256 with PSK, but traffic between the networks isn’t flowing even though the tunnel is up. I will triage quickly by confirming Phase 1/2 settings and PSK alignment on both devices, mapping the exact on-site and remote subnets, and ensuring the traffic selectors match. I will audit route tables, NAT rules, and firewall policies on both sides, verify whether the tunnel is policy- or route-based, and apply precise corrections. After implementing the fix, I will test with ping and traceroute, document the changes, and leave you with a clear plan to prevent regressions. Could you share the current IPSec tunnel configuration (Phase 1/2, PSK, and the exact subnets on each side) and confirm whether there are overlapping networks, so I can diagnose the traffic flow issue?

@ramygoda1590

Hi there, I am networking expert specialist and consultant for more than 11 years, who spend my free time to learn about new technologies in networking, security field to be always up to date. please just ping me on chat to have a short discussion on your project i will always look for solving your tasks ickly. below is a brief on my experience: Technology Specialist: --------------------- - Can design, implment large scale networking and make exaplanation reports. - Practice on Cisco Packet Tracer, GNS-3, EVE-NG. - Excellent pracitce on VMware WorkStation, Virtual-Box - VPN (IPSEC,IKE v1 or v2 ,L2TP ,OPENVPN, DUO Authentication). - Routing Protocols (BGP, OSPF, EIGRP .. ). - Wrie Technical Reports with excellent and format. Skills and Hands on Experience: ------------------------------- - Cisco devices (routers, switches), routing protocols, IPSEC, Cisco ASA Firewall. - Fortinet Devices: FortiGate, Forti Manager, Forti Analyzer. - wireless (WLC, Access Points): CISCO, Aruba, ubiquiti. - Juniper (M7, M10, MX 480, MX 960) and SRX (300, 500). - Operating Systems: Linux servers (Ubuntu, RedHAT, Debian), windows (Windows server 2012, 2016 ..etc). Regards, Ramy

@zulqrn

Hi there, I have solid hands on experience in setting up site-to-site IPSec VPN's for different vendor device and would like to assist you in this. Please drop me a text in chat box to discuss further. I hope to talk to you soon. Thank you!

@Shrutibimpl

Hello, I will troubleshoot and resolve the traffic flow issue on your existing Site-to-Site IPSec VPN between the Cisco ASA and the Ubiquiti Dream Machine Pro (UDM Pro). My focus will be on diagnosing the misconfigurations that are preventing traffic flow, even though the tunnel is established. I will inspect the Access Control Lists on the ASA and the firewall rules/policy routes on both devices to ensure correct NAT exemption (or crypto map application) and verify that the AES-256 encryption and PSK authentication are being correctly negotiated and applied to the traffic from both subnets. 1) What are the local and remote subnets defined in the crypto map/tunnel policy on both the ASA and the UDM Pro? 2) Which specific software version is currently running on the Cisco ASA? 3) Are you able to successfully ping the tunnel interface (or the remote gateway) from both sides when the tunnel is up? Thanks, Bharat

@gobycgd

Hello, I am a certified network engineer and I can help you with your project. I have experience with both Cisco ASA and Ubiquiti UDM Pro. Please contact me to discuss more about your project. Kind regards, Gabriel

@najibe1

Hello, I’m an IT expert with over 20 years of experience in the industry. I hold certifications as a Cisco Certified Networking Professional (300-100 and 300-115), Linux Certified Professional (LPI 101, 102, 103), Red Hat Certified System Administrator, VMware Certified Professional (versions 4, 5, and 5.5), as well as being a Microsoft System Administrator/Engineer from 2003 to 2022 and AZ104 .feel free for any question

@Kierenbennett

Hi, I’d be happy to help with this. I’m an experienced network engineer and IT consultant with strong hands-on experience working with UniFi environments, including the UDM Pro. Over the last year, I’ve migrated more than 10 client networks from a variety of different router and firewall platforms over to UniFi, setting up secure site-to-site and remote VPNs as part of those projects. While I don’t work with Cisco ASA devices on a daily basis, I do have practical experience with Cisco equipment and, more importantly, a lot of experience configuring and troubleshooting VPNs between different vendors. In situations where a VPN tunnel is established but traffic isn’t flowing, the issue is almost always related to routing, firewall rules, or how the two devices handle traffic rather than the VPN itself. I’m used to working in live business environments where stability and clear communication are important, and I’m confident I can get traffic flowing cleanly between the two networks and explain exactly what the issue was and how it’s been resolved. Happy to review the setup and get started straight away. Best regards, Kieren Orb IT Services

@Joejoe777

Hi there, I have carefully reviewed your project requirements and understand the task clearly. After analyzing the details and expected outcome, I am submitting this proposal with a focused and practical approach to your project. For the IPSec VPN setup with Cisco ASA and UDM Pro, I propose to: 1. Investigate the current VPN tunnel setup to identify the issues causing traffic flow problems. 2. Analyze the Cisco ASA and UDM Pro configurations to ensure proper IPSec implementation with AES-256 encryption. 3. Troubleshoot and rectify any misconfigurations affecting the VPN connectivity. 4. Test the VPN tunnel thoroughly to ensure seamless traffic flow between the two networks. This approach ensures a systematic resolution of the traffic flow issues and guarantees a secure and efficient VPN connection. Let's discuss in detail through chat.

@ticketdesk

I come from a rich back ground into networking field handling various such issues on day to day basis - I can help you set this up as quickly as possible

@Jafferi12

That specific issue where the tunnel is up but traffic is dead is the classic Cisco ASA headache. Since your Phase 1 and Phase 2 are connecting, your keys and encryption are perfect. The problem is almost certainly how the Cisco ASA is tagging the traffic internally before it hits the VPN tube. The router is likely trying to send that private traffic out to the public internet by mistake. I handle this exact setup often. I will jump into the CLI, run a packet trace to see exactly where the drop is happening, and fix the routing logic without breaking your internet connection. Since I have a background in security, I will also make sure the firewall rules on the UDM side aren't silently dropping the packets coming back. I am ready to knock this out right now. Let’s look at the logs.

@TomaK01

As a Senior Full-Stack Software Engineer with over 20+ years of coding experience, I possess a unique blend of skills that align perfectly with your project requirements. Though my profile may not emphasize network administration, during my extensive career, I've navigated numerous complex technical issues ranging from web scraping to implementing secure cloud-based solutions like yours. This diverse background has given me the ability to not only learn quickly but also solve problems creatively even within unfamiliar domains. Being adaptable and solution-oriented, I'm confident that I can help resolve your VPN tunneling problems. My familiarity with encryption methods, including AES-256 and protocols like IPSec, combined with my knowledge of Cisco ASA and UDM Pro routers uniquely position me to swiftly identify and rectify any configuration or compatibility issues occurring between them. Moreover, as an experienced freelancer, I know the value of clear and transparent communication. I'll provide you with a detailed plan for troubleshooting the existing problem while simultaneously ensuring your existing configuration retains its useability. Finally, as someone who values not just the completion of projects but their overall success, you have my commitment to remain available even after the project is completed to address any follow-up concerns or optimization needs. Thank you for considering me for this project

@robertc167

I am a seasoned Technology Architect based in Lisbon, Iowa, with a distinguished record of over a decade designing, deploying, and managing advanced network and cloud infrastructure. I currently serve as a Technology Architect at ark data centers, where I bring over nine years of experience as a Network Architect and Cloud Infrastructure Engineer within the same organization. I also spent many years at Involta, contributing as both a Network Engineer and Data Center Manager, building expertise in network security, Linux systems, and large-scale data center operations. I hold a Master of Science in Information Assurance from Capella University and a Bachelor’s in Management Information Systems from Iowa State University. I am certified as a VMware Certified Professional and Cisco CCNP Enterprise. My core competencies include VMware NSX, network engineering, cloud architectures, BGP, and information security, making me a trusted expert for designing resilient, cutting-edge infrastructure in hybrid environments.

@LeoMelo2025

With 35 years of experience as a Senior Systems Engineer and Consultant, I am exceptionally qualified to tackle your IPSec VPN setup project. From managing information technology to guiding telecommunication services, I've cultivated extensive knowledge in network security and administration, primarily focusing on vital areas like Data centers, infrastructure, and security projects. Cisco ASA and UDM Pro are familiar territory for me, as I have hands-on expertise with these systems from my work with various companies including Cisco itself. I have configured IPSec VPNs in a myriad of scenarios and understand the complexity involved in establishing secure connections that enable smooth traffic flow between networks. Troubleshooting VPN issues is second nature to me. I will conduct a detailed examination of your existing setup, considering the AES-256 encryption and pre-shared key authentication requirements you've stated, to diagnose and resolve the traffic issue currently impeding your VPN tunnel. Throughout my career, I've always approached each task methodically and efficiently; planning and strategy are my strong suits. My focus lies not only on executing projects but ensuring they align with long-term business strategy. You can expect meticulous problem-solving skills, methodical planning and comprehensive system knowledge.

@shamraiz85

I am a Senior Network Engineer with over 15 years of enterprise-level experience in network security, firewall management, and site-to-site IPSec VPN implementations. I have delivered and supported mission-critical VPN solutions for banking and financial environments, where strong encryption, high availability, and zero downtime are mandatory. I have deep hands-on expertise with Cisco ASA and Ubiquiti Dream Machine Pro (UDM Pro), and have designed, implemented, and troubleshot numerous IPSec VPN deployments using AES-256 encryption and pre-shared key (PSK) authentication, following industry best practices and security standards.

@elhaquilamyaa

Hello, I have strong hands-on experience designing, deploying, and troubleshooting IPSec site-to-site VPNs across mixed vendor environments, including Cisco ASA and Ubiquiti UDM Pro. Since the tunnel is already established but traffic is not flowing, this is typically related to Phase-2 selectors, NAT-exemption, routing, or ACL filtering rather than encryption settings. My Troubleshooting & Remediation Approach Verify Phase-1 / Phase-2 parameters and ensure full parity (AES-256, PSK, DH group, lifetime) Review and align Proxy-IDs / Local–Remote subnet definitions Check NAT-Exemption / No-NAT rules on the ASA and UDM Pro Validate security-policies / ACLs affecting inter-site traffic Confirm routing paths and prevent asymmetric flows Inspect IPSec SA counters and packet statistics (show crypto ikev2 sa, show crypto ipsec sa, packet-trace) Run controlled end-to-end tests (ICMP / host-to-host / subnet-to-subnet) Apply corrective changes and re-validate bidirectional connectivity Experience Cisco ASA (crypto-map / tunnel-group / policy-based & route-based VPNs) Ubiquiti UDM Pro IPSec & network policies Multi-vendor VPN interoperability and NAT/routing design Production network troubleshooting and change-safe implementation I’m available to start immediately and can work through a secure remote session while coordinating live testing. Best regards,

@keaganhaynes14

I am a strong fit for your project. I understand that you need help specifically with ensuring proper traffic flow between two networks over a site-to-site IPSec VPN using a Cisco ASA router and a Ubiquiti Dream Machine Pro, and my focus is delivering a clean, professional, and seamless solution that works reliably. I specialize in building user-friendly, integrated, and automated network configurations, prioritizing clear communication and practical results. While I am new to Freelancer, I have extensive real-world experience configuring secure IPSec VPNs with AES-256 encryption and PSK authentication, having completed multiple projects outside the platform. Do you already have a preferred timeline or specific tools you’d like me to work with? I would love to chat more about your project! Regards, Keagan

@thanhnguyen1997d

am a versatile Systems Engineer with extensive experience in Networking (CCNA & Juniper certified) and enterprise infrastructure. I specialize in deploying and managing complex systems, including ERP solutions, Active Directory (AD), and mail servers. My expertise extends to full-cycle implementations of Web Panels, hosting environments, and cloud infrastructures within large-scale corporate settings. I have a proven track record of integrating seamless communication systems and ensuring high-performance hosting availability. With a deep understanding of both hardware and software layers, I am ready to provide end-to-end technical solutions for your project. I look forward to contributing my technical leadership to your team's success