A script that cycles through 25 password changes to clear your password history.

cycle_passwords.exp

#!/usr/bin/expect -f

# Script to cycle through password history on macOS
# Usage: ./cycle_passwords.exp <current_password> <target_password>

if {$argc != 2} {
    puts "Usage: $argv0 <current_password> <target_password>"
    puts "This script will change your password 25 times to clear history,"
    puts "then set it to your target password."
    exit 1
}

set current_pass [lindex $argv 0]
set target_pass [lindex $argv 1]
set username [exec whoami]

# Generate 24 temporary passwords (we'll use target as #25)
proc generate_temp_password {index} {
    return "TempPass${index}![clock seconds]"
}

puts "========================================="
puts "Starting password history cycling for user: $username"
puts "This will perform 25 password changes"
puts "========================================="
puts ""

set timeout 10

# Function to change password
proc change_password {old_pw new_pw iteration} {
    global username
    
    puts "Attempt $iteration/25: Changing password..."
    puts "  New password: $new_pw"
    
    spawn passwd
    
    expect {
        timeout {
            puts "ERROR: Timeout waiting for Old Password prompt"
            exit 1
        }
        "Old Password:" {
            send "$old_pw\r"
        }
    }
    
    expect {
        timeout {
            puts "ERROR: Timeout waiting for New Password prompt"
            exit 1
        }
        "New Password:" {
            send "$new_pw\r"
        }
    }
    
    expect {
        timeout {
            puts "ERROR: Timeout waiting for Retype New Password prompt"
            exit 1
        }
        "Retype New Password:" {
            send "$new_pw\r"
        }
    }
    
    # Wait for the warning message and command completion
    expect {
        timeout {
            puts "ERROR: Timeout waiting for completion"
            exit 1
        }
        -re ".*WARNING.*" {
            # Got the keychain warning, wait for prompt to return
            expect {
                -re "\[#$%>\] $" {
                    # Back at shell prompt
                }
                timeout {
                    # Warning displayed but prompt detection failed, that's ok
                }
            }
        }
        -re "\[#$%>\] $" {
            # Back at shell prompt (in case warning doesn't appear)
        }
    }
    
    # Small delay to ensure change is committed
    sleep 0.5
    
    puts "  ✓ Successfully changed (iteration $iteration)"
    puts ""
    
    return $new_pw
}

# Perform 24 intermediate changes
for {set i 1} {$i <= 24} {incr i} {
    set temp_pass [generate_temp_password $i]
    set current_pass [change_password $current_pass $temp_pass $i]
}

# Final change to target password
puts "Final change (25/25): Setting to target password..."
puts "  New password: $target_pass"
change_password $current_pass $target_pass 25

puts ""
puts "========================================="
puts "SUCCESS: Password history cleared"
puts "Your password is now set to: $target_pass"
puts "Entra sync should now succeed"
puts "========================================="
puts ""
puts "NOTE: The login keychain password was NOT updated by this script."
puts "If needed, run: security set-keychain-password"

exit 0