A Dante-inspired descent through app discovery, SaaS jungle vines, legacy monsters, ancient databases, cloud review tribunals, and the eternal budget question: who pays for this?
Each circle is guarded by a different enterprise demon. Some breathe fire. Others ask for the application inventory in a different spreadsheet template.
You begin with “just send us your app list.” They send a spreadsheet with 412 rows, 97 blanks, 31 duplicates, and one entry simply called “The System.” Half the owners are “TBD.” The other half are Dave, who retired in 2018.
Every department bought its own tool. Every tool has its own admin. Every admin left. Billing goes to a shared mailbox nobody monitors, and the recovery email is steve@oldcompany.com.
The app requires Internet Explorer mode, Java 6, a mapped drive, a domain admin service account, and a specific printer named Accounting_HP_Do_Not_Delete. The vendor calls it “stable.” You call it haunted.
Windows Server 2008, SQL Server 2012, Oracle 9i, Access, FoxPro, and one beige physical server making a noise like a haunted leaf blower. Someone whispers, “Do not reboot that.” Nobody knows why. Everyone obeys.
You have a clean Azure design. Then the guardians appear: Security, Network, Architecture, Data Privacy, Compliance, Procurement, and “just one more reviewer.” Each approval reveals two more approvals beneath it.
The migration needs hosting, licenses, vendor hours, storage, support, and maybe a small sacrifice to the VPN gods. Corporate says it is project cost. The business says it is IT cost. Finance says, “Can you split it by app?”
DNS is ready. SSO is ready. Data is staged. Everyone says “go.” Then one user finds a macro-enabled workbook that writes to production through an ODBC connection named Bob_Local_Final. The bridge collapses. The war room awakens.
Artifacts recovered from previous migrations. Handle carefully. Most contain macros.
Last updated by “admin” in 2014. Contains one useful sentence: “Ask Dave.” Dave is gone.
A sacred Excel workbook protected by a password nobody remembers. It contains all other passwords.
Signed by someone who left before the acquisition was announced. Renewal auto-bills forever.
Requires Internet Explorer, Java 6, TLS 1.0, a domain admin service account, and emotional support.
HP: ∞ • Hardcoded IP addresses • Production database named TEST_NEW_FINAL • Service account password expires during cutover • Vendor says cloud version is “on the roadmap” • Runs payroll, invoicing, and one mystery button no one clicks Weakness: None discovered.
Press the button to receive a cursed executive prophecy.
Applications Discovered: 412 Applications Originally Listed: 37 Unexpected Vendors: 31 Emergency Meetings: 87 “Quick Questions”: 493 Legacy Servers Named PROD2: 9 Coffee Consumed: Infinite Documentation Created: Finally Status: COMPLETE Next Event: NEW ACQUISITION KICKOFF — MONDAY 8:00 AM