Proprietary Estoppel – Building the Narrative and Testing the Evidence

Introduction

1. This year I have had the pleasure of working on various cases involving the doctrine of proprietary estoppel from pre-action advisory stages right through to trial (whether on behalf of the Claimant or the Defendant). As any legal professional specialising in property litigation will attest to, not many claims of proprietary estoppel reach trial given the inherent uncertainty involved in the relief the Court may award in its discretion and the lack of documentary evidence in support of such a claim (such cases resting, by and large, on oral evidence). Advising a client to undertake mediation and settle such claims is both common and understandable in these circumstances.
   
2. However, utilising my experience from this year, there are some practical and tactical tips available to help legal practitioners assess the prospects of success in running such a claim or a defence against such a claim and to run such claims and defences effectively. This is particularly important when dealing with parties, especially family members at war, holding entrenched positions with both parties confidently asserting they are right about their version of events. It is important to find a way to cut through the noise and understand the reality of the client’s position.
   
3. This article is therefore aimed at providing some practical and tactical tips I have unearthed this year whilst running heated proprietary estoppel cases involving family members at war. The article assumes a working knowledge and understanding of the law of proprietary estoppel by the reader. It is not a summary of the law or a legal update but a practical guide for the legal practitioner in dealing with such cases.

The Case Narrative

4. In deciding whether to run or challenge a proprietary estoppel claim and do so effectively, it is important that the client presents a viable and consistent version of events. As a barrister, the development of a case theory is a fundamental requirement when preparing for trial. However, for any legal practitioner dealing with a claim in proprietary estoppel, it is vital that the client’s version of events is put together at the earliest opportunity (ideally pre-action) and then tested by reference to the other side’s position (if known) and the documentary evidence available at the time.
   
5. This might be a point that holds true for any type of litigation but particularly so for claims in proprietary estoppel because it is likely that the purported promise or the meeting where the said promise was purportedly made goes back in time a long way, maybe even decades. The case will therefore heavily rely on memory and oral evidence and therefore the testing of the client’s narrative is essential. This will alert the client to the blind spots in their case at the earliest possible stage enabling the client to understand the risks involved in pushing their case forwards and/or the next steps to be taken to prepare the case.
   
6. Many proprietary estoppel cases involve an intimate or personal setting where one family member is said to have promised something to another and that other family member is said to have detrimentally relied upon that promise over time. This lends well to effective storytelling. The aim for the legal practitioner is to therefore present their client’s story to the Court in the most simple and effective way possible in the witness evidence (in chronological order with emphasis placed on key periods of time and by reference to the three key elements of promise, reliance and detriment). The supporting documentary evidence should aid the story being told. This will not only assist in the assessment of prospects of success as the case progresses but also the Court, and the barrister in presenting the case, at trial.
   
7. The testing of the client’s narrative goes hand in hand with assessing the narrative of the other side too. Further, the more compelling, clear and logically consistent the story then, subject to the oral evidence given at trial, the better the chances of persuading the Court of the client’s position. The less compelling, clear and logically consistent the story then the case may be one that requires settling at the earliest opportunity.
   
8. As a final point, the net should be cast out wide when it comes to telling the client’s story. The context and background to the client’s version of events (e.g. their relationship with the other party or witnesses or their activities before and after any key periods of time or events) may prove pivotal in a proprietary estoppel case. This is because it will assist the Court (and the legal practitioner when testing their client’s case) in determining the probabilities of the client’s version of events being the correct one. The caveat to this is that the context and background should be relevant. The written evidence is not an autobiography.

The Documentary Evidence

9. In a proprietary estoppel case no one piece of documentary evidence is likely to be a killer blow (there is unlikely to be a napkin signed and dated by the said promisor with the promise written on it).
   
10. It is therefore worth carefully examining each document disclosed by the client and the other side to see if it adds value or hurts the client’s case (i.e. does the document expand or cement the client’s story or does it go against the story). The evidence may take the form of the contents of various historic wills and letters of wishes or even photographs of what appears to be a happy family at a birthday party. These were some of the types of evidence I had encountered this year in my proprietary estoppel cases.
    
11. In light of the ongoing duty of disclosure, it is important to keep an eye on disclosure developments as the directions timetable progresses. This might necessitate the need to consider settlement (if significantly enhancing or undermining prospects of success), or the need for permission to rely on further witness evidence to explain away the disclosure or even the amendment of pleadings depending on the bearing the additional disclosure has upon the parties’ narratives.
    
12. Whilst proprietary estoppel claims will rely, largely, on oral evidence given at trial, the above demonstrates why documentary evidence has an important role to play in such cases, particularly contemporaneous documentary evidence. Such documents play an important part in establishing the truth.[1] Indeed, as Lord Bingham has stated, “in this process of establishing the truth, compulsory disclosure plays a crucial part. Letters, diary entries, memos and minutes made or written at the time often provide a surer guide to the truth than what the participants say years later when differences have arisen.[2]” This statement holds absolutely true when it comes to proprietary estoppel cases. Contemporaneous documentary evidence helps establish the story being told and places the witnesses’ recollections and evidence in context, assisting in the process of cross-examination.[3]
    
13. However, to help assess prospects of success or prepare the client’s case effectively, the following principles ought to be borne in mind when assessing the documentary evidence (which the Trial Judge will have in mind when assessing the evidence in any event):-

1. Just because something is recorded in a document does not necessarily mean it is true or accurate. Thus when a note of a meeting has been created, the accuracy will depend on how detailed it is and what facts the maker may have decided or remembered at the time to note down. At meetings a statement may not seem significant or even have been heard or remembered by the time the note was prepared;
   
2. The interests and possible motives of the maker may be relevant. A party may write a letter setting out his position to the other party. That does not mean what is stated in the letter is true. However, if the other party replies and either refutes an assertion of fact or replies and expressly accepts it or simply does not reply at all, that may be highly relevant. Thus looking at one document in isolation may give a wrong impression. A document should be considered in the context of other documents as well as any witness evidence relating to it;
   
3. Documents get lost, mislaid and destroyed, thus the documents before the Court may not show the complete picture;
   
4. Where what is stated or recorded in a document is in dispute, then the Court should consider the circumstances of its creation, possible reasons why it may be inaccurate, and the motives and interests of the maker; and
   
5. There is no fixed rule or presumption that documentary evidence is always to be preferred to the evidence of the witnesses to which it may conflict. There may be circumstances in which the documents can be shown to be inherently unreliable or the oral evidence may throw an entirely different light on the apparent meaning of a document.[4]

14. The above demonstrates that, in a proprietary estoppel case, blind reliance cannot be placed on any contemporaneous documentary evidence. However, given that the relevant events in a proprietary estoppel case may have taken place years ago, there will likely have been a deterioration in witness recollection and therefore the contemporaneous documentation, if any, is still going to play a crucial role in the outcome of such a case (along with the inferences drawn from this evidence). However, the legal practitioner must remain conscious of self-serving documentary evidence and the fact that not all contemporaneous documentary evidence will hold the same weight.
    
15. I would ask legal practitioners testing their client’s proprietary estoppel case or the other side’s proprietary estoppel case by reference to documentary evidence (whether pre-action or as the directions timetable progresses) to bear in mind and utilise the crucial principles on witness recollection and documentary evidence summarised from prior authority in The Queen on the application of Dr Ashish Dutta v GMC [2020] EWHC 1974 at [39]-[42]. For reasons of brevity, I do not set out all the principles here save for the following (which again the Trial Judge would have in mind when assessing the evidence):-

1. The best approach from a Judge is to base factual findings on inferences drawn from documentary evidence and known or probable facts. This does not mean that oral testimony serves no useful purpose but its value lies largely in the opportunity which cross-examination affords to subject the documentary record to critical scrutiny and to gauge the personality, motivations and working practices of a witness, rather than in testimony of what the witness recalls of particular conversations and events. Above all, it is important to avoid the fallacy of supposing that, because a witness has confidence in his or her recollection and is honest, evidence based on that recollection provides any reliable guide to the truth;
   
2. Witnesses, especially those who are emotional, who think they are morally in the right, tend very easily and unconsciously to conjure up a legal right that did not exist. It is a truism that with every day that passes the memory becomes fainter and the imagination becomes more active. For that reason, a witness, however honest, rarely persuades a Judge that his present recollection is preferable to that which was taken down in writing immediately after the incident occurred. Therefore contemporary documents are always of the utmost importance; and
   
3. Oral evidence under cross-examination is far from the be all and end all of forensic proof as a result.

16. In light of the above, the legal practitioner should, at the appropriate time in the litigation, test the written evidence (particularly the known or probable facts) against the documentary record in analysing the strengths and weaknesses of the case. This will anticipate the likely outcome at trial. This may also be an exercise for a barrister to perform when advising on merits and settlement prior to trial.

Reverse Engineering the Process

17. The aforementioned practical and tactical tips relate more to the first limb in proprietary estoppel, namely the promise or representation. Usually the detrimental reliance will be significantly easier to establish by way of evidence: the Claimant may have spent millions of pounds on developing the property which is the subject matter of the case or consciously missed out on other life opportunities in order to promote a business, all in the name of the promise made. Prima facie, it would appear that if the evidence shows that significant funds were spent on developing the property or a person did miss out on numerous life opportunities over a significant period of time, the promise must have been made. Why else would someone have done that?
    
18. The aforementioned logic does not always stand up to scrutiny and particularly when acting for the Defendant it is worth undertaking a reverse engineered analysis of the proprietary estoppel claim at the earliest opportunity and throughout the directions timetable particularly post disclosure. Does the documentary evidence support the detrimental reliance or are there gaps in the evidence? Could the so called detriment be explained away by other motivations of the Claimant and is there any evidence to support those other motivations? If one is acting for the Claimant the analysis may take the form of ensuring the evidence does stand up to scrutiny and there is no other reason why the detriment has been suffered.
    
19. The process of analysis undertaken above may assist in testing the probabilities of the promise having been made and also help in the presentation of the case to the Court.

Countervailing Benefits

20. An easily forgotten point but worth keeping in mind is that, in considering what detriment the Claimant has suffered, the Court will take into account any countervailing benefits the Claimant has received from the Defendant (e.g. significant rent free occupation). In those circumstances a Court may hold that it is not unconscionable for the Defendant to insist on their strict legal rights. Whilst not a conclusive point as the Court undertakes a broad enquiry when analysing the limbs of proprietary estoppel, depending on the extent of the countervailing benefit and the particular facts of the case, this may prove to be a factor of importance. It is therefore a factor for the legal practitioner to examine and keep in mind.

Conclusion

21. At its core, a proprietary estoppel claim (or a defence against such a claim) succeeds or fails on the credibility of the story being told, and the discipline with which that story is tested against the evidence. If practitioners interrogate their client’s narrative early and continuously throughout the litigation, particularly by reference to contemporaneous documentary evidence and they remain alert to any alternative explanations for the detriment said to have been suffered (or any countervailing benefits), the fog of uncertainty that usually surrounds these types of cases can begin to clear. This may assist in positioning the client in a favourable position for settlement but, if required, also for trial.

Mr Raghav Trivedi, 9 December 2025

[1] Phipson on Evidence, 20^th Edn, para 45-29

[2] Matthews and Malek, Disclosure, 2^nd Edn, Foreword

[3] Phipson on Evidence, 20^th Edn, para 45-30

[4] Phipson on Evidence, 20^th Edn, para 45-31

Whilst every effort has been taken to ensure that the law in this article is correct, it is intended to give a general overview of the law for educational and/or informational purposes. It is not intended to be a substitute for specific legal advice and should not be relied upon for this purpose.

This article represents the opinion of the author and does not necessarily reflect the view of any other member of St Philips Chambers.