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Hey, This trophy took me a while to get as I didn't know what I was doing wrong, I eventually discovered how and thought I'd make an in depth as I can guide for it. Before doing this trophy, Obviously join the guild in riften and once you receive your armour from tonillia NEVER get rid of it! it is vital to get the final trophy.
The first, and easiest, is to finish the main story, every single quest in it.
A Chance Arrangement
- Taking Care of Business
- Loud and Clear
- Dampened Spirits
- Scoundrel's Folly
- Speaking With Silence
- Hard Answers
- The Pursuit
- Trinity Restored
- Blindsighted
- Darkness Returns
Now once you have completed these you will need to do 5 or 4 Jobs in every main city in Skyrim, Whiterun , Windhelm , Solitude and Markarth.
(Riften is not needed as you already have a thieves guild present in the city.
To get these jobs speak to either Delvin or vex, both offer different jobs and the city in which you do the job is randomly generated.
<b>

elvin will offer the following types of mission:</b>
- The Bedlam Job: Rob a certain city for (X) amount of loot.
- The Fishing Job: Steal an item right from a target's pocket.
- The Numbers Job: Change the numbers in a book keepers book.
<b>Vex will offer the following types of mission:</b>
- The Burglary Job: Retrieve a special item for a client
- The Shill Job: Plant evidence against a target.
- The Sweep Job: Rob a house of several specific valuables.
- The Heist Job: Steal a particular item from a shop.
Each mission must also be completed without you killing any residents of the city, or getting caught and having to spend time in jail. The location for each city is randomly generated. Fortunately, if you save before talking to either Vex or Devlin, you can reload if you are asked to go to a city where you have already completed 5 jobs there.
Once you finish 5 jobs in a city, you'll be given one of the following quests by Devlin - relating to the city with the jobs:
Imitation Amnesty: – Whiterun
Silver Lining: - Markarth
Summerset Shadows: - Windhelm
The Dainty Sload: - Solitude
After each of these quests is completed, you'll notice that the Thieves Guild improves slightly. You'll also be able to upgrade your Thieves Guild armor after each mission - this is why you must hold onto the lot until you have this trophy. If you have sold any of the armor, or lost it, then you'll need to reload an earlier save where you still have the gear, or restart.
If you get a job in a location you have already done the special for, just cancel the job, there will be no penalty for this, you just get groaned at by Vex or Devlin, saves your time doing pointless jobs.
Once you've done all of the above quests, speak to Brynjolf about becomming the next Guildmaster, he will give you instructions on what to do and you will get brand new guild master armour

and the trophy of course :p.
pls respond if you need help.