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I have drafted this cover letter based on the requirements for settlement applications in 2020 AND an earlier template letter by @marcnath for initial T1E applications (which I had found to be VERY helpful). I will welcome comments from anyone and hope this helps someone else as well who applies for ILR after me. Fingers crossed on my application now, as I plan to submit this by end of this week. In my specific circumstance I am registered both as Dir of a ltd. company as well as self-emp (I will include a note to explain this).

Dear Sir/Madam,
Enclosed is the application for my ILR. I believe this application is straightforward, whereas I encompass this cover letter as per Tier 1 (Entrepreneur) Policy Guidance – version 1 0 /2019 – Page 10 to make it as succinct and clear as possible.

1. Investment activity – I wish to claim 20 points for having invested the sum £50,000 in a UK business. I am claiming exemption from providing evidence, as per Row 1 of Table F in guidance notes which states: “You do not need to provide evidence of this investment if you were awarded points for this investment in your last successful Tier 1 (Entrepreneur) application.”. As someone with the last permission as a Tier 1 (Entrepreneur) Extension visa, I would like to claim the points for this without providing further evidence.

2. Business activity - I wish to claim 20 points for my business activities in the UK based on (i) registered with HMRC/ Companies House and (ii) remained registered in the last three months. I am claiming exemption from providing evidence, as per Row 2 of Table F in guidance notes which states: “You do not need to provide evidence of (i) if you were awarded points for this in your last successful Tier 1 (Entrepreneur) application. You must still provide evidence of (ii).”. I attach the CAR (Current Appointments Report) of Connect-In Ltd that shows I have been the founding Director of the company and remain a Director on 14/08/20 (date of report generation). I also enclose tax document showing two UTRs (one as ltd. director and other as self-employed).

3. Job Creation - My company divisions have had 11 FT employees on payroll and other contract-based or PT workers through the period of my stay in the UK as a Tier-1 Entrepreneur. Under the rules, I would like to claim 20 points for the 2 most recent job posts created in the past 12 months. As evidence, I provide 1. Staff member IDs (biometric passport page); 2. Employee Hours & Payscale 3. RTIs (Last 12 Months) 4. Employees Payslips (Last 12 Months) along with their P60’s, P45s (of employees who left).

4. Legal stay – I would like to claim 15 points under part 4 (a) that state, “You have spent a continuous period of 5 years lawfully in the UK with leave as a Tier 1 (Entrepreneur) migrant”, I have enclosed a copy of both my previous Leave To Remain as Tier-1 Entrepreneur migrant.

5. LIUK Test & English Language – I have been able to book the LIUK test at DATE (earliest available date) and will be uploading a pass certificate/ number as soon as I am able to pass the test. I also enclose my degree certificate from the University of XX, should English Language requirement need to be verified.

I am surprised much less docs were asked this time compared to extension applications. Eg. trading activity proof was not asked specifically? I plan to include it as below still along with the consent for verification checks.
Enclose:
- Financial Statements for the most recent FYE Jun 2020; - Most recent Business Bank Statements (XX Banks), 30 days generated 17 Aug 2020; – Personal Bank Statement, 30 days, generated 17 Aug 2020.

NOT Including (as was already included in previous applications to prove Genuine Entrepreneur and available again on request)
- Signed agreement/ term sheet of first investment made in my Company in 2013: £XXk - Signed agreement/ term sheet of second investment made in my Company in 2014: £XXk - other press documents, patents, awards, etc (2014- 17) not included again, but included are 2 new business awards 19-20.

I hope this would be sufficient.

As I understood, the key docs needed are:

HM Revenue & Customs documentation to demonstrate your registration
Companies House documentation to demonstrate your registration
Real Time-Full Payment Submissions & docs to prove employees are settled, workers.

"Providing your documents
You must provide your documents after you submit your application, these can be originals or copies. Any passports provided must be originals.".

Although it says passports provided must be original, I believe it is NOT needed to be send in physical copy - correct?

You do not need to send any physical documents to the Home Office or UK Visas & Immigration unless you are advised to do so.

I appreciate you drafting a cover letter, but its not needed if you do not have any exceptional reason to explain. I would urge you to keep your documents simple, to the point as per the guidance. Sending extra documents which are not required are not recommended.

Btw at least one month business bank statement is mandatory. You seem to have included that in optional category.

Also, description regarding employee and director job roles is needed.

Thank you both for the inputs. Yeah, it did not ask/ I could not find the requirement for bank statement but I'll incl. it with docs, thanks.