🕐 Troubleshooting Timeline
Minutes 0-8: Initial Assessment
Problem Identification: Ubuntu VM unable to reach external network despite bridged configuration
Tools Used: Screenshots analysis, VMware settings review, initial ping tests
Discovery: "Destination Host Unreachable" errors indicating Layer 2/3 connectivity issues
Minutes 8-23: Deep Network Analysis
Commands Executed: ip route show, ip neigh show, ip link show
Key Finding: ARP resolution failing for gateway (192.168.88.1 FAILED status)
Approach: Manual static IP configuration using modern Linux networking tools
Minutes 23-31: DNS & systemd-resolved Investigation
Challenge: Encountered systemd-resolved complexity in modern Ubuntu
Learning: /etc/resolv.conf is now managed dynamically, not directly editable
Solution: Used resolvectl commands for proper DNS configuration
Minutes 31-36: Host Network Analysis
Investigation: Windows host ipconfig /all analysis
Validation: Confirmed 192.168.88.x network is correct (host at .226)
Router Access: Checked DHCP lease table to verify IP availability
Minutes 36-39: DHCP Lease Analysis
Professional Approach: Used router admin interface to check lease table
Confirmation: 192.168.88.16 available, no IP conflicts detected
Network Mapping: Identified all active devices on subnet
Minutes 39-47: Scripted Testing Approach
Automation: Created comprehensive bash script for network configuration
Testing: Systematic approach with different IP (.50 instead of .16)
Result: Same connectivity issues, eliminating IP conflict as root cause
Minutes 47-53: Root Cause Analysis
Conclusion: Identified VMware bridged networking as likely culprit
Next Steps: Virtual Network Editor investigation, MAC filtering checks
Documentation: Created this comprehensive troubleshooting report
🎯 Skills Developed & Reinforced
Modern Linux Networking: Transitioned from deprecated ifconfig to ip command suite
systemd Integration: Understanding systemd-resolved and modern Ubuntu networking
Layer 2/3 Analysis: ARP troubleshooting and connectivity layer identification
Systematic Troubleshooting: Methodical elimination of variables and root cause analysis
Script Development: Bash automation for repetitive network configuration tasks
Network Infrastructure: Router administration and DHCP lease management
Virtualization: VMware networking modes and bridged configuration troubleshooting
Documentation: Professional technical communication and problem tracking
💡 Session Outcome
This 53-minute deep-dive troubleshooting session demonstrates advanced networking problem-solving skills and persistence in complex technical challenges. While the immediate connectivity issue requires further VMware-specific investigation, the systematic approach, modern tool usage, and comprehensive analysis showcase significant growth in enterprise-level IT troubleshooting capabilities.
The journey from problem identification to root cause analysis exemplifies the methodical thinking required for senior IT management roles.