diff --git a/Source/aweXpect/That/Collections/CollectionHelpers.cs b/Source/aweXpect/That/Collections/CollectionHelpers.cs
index 7e8efec02..e4e19ef62 100644
--- a/Source/aweXpect/That/Collections/CollectionHelpers.cs
+++ b/Source/aweXpect/That/Collections/CollectionHelpers.cs
@@ -47,15 +47,21 @@ internal static ExpectationBuilder AddCollectionContext<TItem>(this ExpectationB
 		}
 
 		return expectationBuilder.UpdateContexts(contexts
-			=> contexts
-				.Add(new ResultContext("Collection",
-					() => Formatter.Format(value, typeof(TItem).GetFormattingOption(value switch
-					{
-						ICollection<TItem> coll => coll.Count,
-						ICountable countable => countable.Count,
-						_ => null,
-					})).AppendIsIncomplete(isIncomplete),
-					-1)));
+			=>
+		{
+			if (contexts.All(c => c.Title != "Collection"))
+			{
+				contexts
+					.Add(new ResultContext("Collection",
+						() => Formatter.Format(value, typeof(TItem).GetFormattingOption(value switch
+						{
+							ICollection<TItem> coll => coll.Count,
+							ICountable countable => countable.Count,
+							_ => null,
+						})).AppendIsIncomplete(isIncomplete),
+						-1));
+			}
+		});
 	}
 
 	internal static ExpectationBuilder AddCollectionContext(this ExpectationBuilder expectationBuilder,
@@ -77,15 +83,21 @@ internal static ExpectationBuilder AddCollectionContext(this ExpectationBuilder
 		}
 
 		return expectationBuilder.UpdateContexts(contexts
-			=> contexts
-				.Add(new ResultContext("Collection",
-					() => Formatter.Format(value, type.GetFormattingOption(value switch
-					{
-						ICollection coll => coll.Count,
-						ICountable countable => countable.Count,
-						_ => null,
-					})).AppendIsIncomplete(isIncomplete),
-					-1)));
+			=>
+		{
+			if (contexts.All(c => c.Title != "Collection"))
+			{
+				contexts
+					.Add(new ResultContext("Collection",
+						() => Formatter.Format(value, type.GetFormattingOption(value switch
+						{
+							ICollection coll => coll.Count,
+							ICountable countable => countable.Count,
+							_ => null,
+						})).AppendIsIncomplete(isIncomplete),
+						-1));
+			}
+		});
 	}
 
 #if NET8_0_OR_GREATER
@@ -98,12 +110,18 @@ internal static ExpectationBuilder AddCollectionContext<TItem>(this ExpectationB
 		}
 
 		return expectationBuilder.UpdateContexts(contexts
-			=> contexts
-				.Add(new ResultContext("Collection",
-					() => Formatter.Format(value.MaterializedItems,
-							typeof(TItem).GetFormattingOption(value.Count))
-						.AppendIsIncomplete(isIncomplete),
-					-1)));
+			=>
+		{
+			if (contexts.All(c => c.Title != "Collection"))
+			{
+				contexts
+					.Add(new ResultContext("Collection",
+						() => Formatter.Format(value.MaterializedItems,
+								typeof(TItem).GetFormattingOption(value.Count))
+							.AppendIsIncomplete(isIncomplete),
+						-1));
+			}
+		});
 	}
 #endif
 
@@ -116,11 +134,17 @@ internal static ExpectationBuilder AddCollectionContext<TKey, TValue>(this Expec
 		}
 
 		return expectationBuilder.UpdateContexts(contexts
-			=> contexts
-				.Add(new ResultContext("Dictionary",
-					() => Formatter.Format(value, typeof(TValue).GetFormattingOption(value.Count))
-						.AppendIsIncomplete(isIncomplete),
-					-2)));
+			=>
+		{
+			if (contexts.All(c => c.Title != "Dictionary"))
+			{
+				contexts
+					.Add(new ResultContext("Dictionary",
+						() => Formatter.Format(value, typeof(TValue).GetFormattingOption(value.Count))
+							.AppendIsIncomplete(isIncomplete),
+						-2));
+			}
+		});
 	}
 
 	internal static ExpectationBuilder AddCollectionContext<TKey, TValue>(this ExpectationBuilder expectationBuilder,
@@ -132,11 +156,17 @@ internal static ExpectationBuilder AddCollectionContext<TKey, TValue>(this Expec
 		}
 
 		return expectationBuilder.UpdateContexts(contexts
-			=> contexts
-				.Add(new ResultContext("Dictionary",
-					() => Formatter.Format(value, typeof(TValue).GetFormattingOption(value.Count))
-						.AppendIsIncomplete(isIncomplete),
-					-2)));
+			=>
+		{
+			if (contexts.All(c => c.Title != "Dictionary"))
+			{
+				contexts
+					.Add(new ResultContext("Dictionary",
+						() => Formatter.Format(value, typeof(TValue).GetFormattingOption(value.Count))
+							.AppendIsIncomplete(isIncomplete),
+						-2));
+			}
+		});
 	}
 
 	internal static string AppendIsIncomplete(this string formattedItems, bool isIncomplete)
diff --git a/Tests/aweXpect.Tests/Collections/ThatAsyncEnumerable.Contains.Tests.cs b/Tests/aweXpect.Tests/Collections/ThatAsyncEnumerable.Contains.Tests.cs
index 9dc24989a..9961d45ef 100644
--- a/Tests/aweXpect.Tests/Collections/ThatAsyncEnumerable.Contains.Tests.cs
+++ b/Tests/aweXpect.Tests/Collections/ThatAsyncEnumerable.Contains.Tests.cs
@@ -339,6 +339,29 @@ Expected that subject
 					             but it was <null>
 					             """);
 			}
+
+			[Fact]
+			public async Task WithMultipleFailures_ShouldIncludeCollectionOnlyOnce()
+			{
+				IAsyncEnumerable<string> subject = ToAsyncEnumerable(["a", "b", "c",]);
+
+				async Task Act()
+					=> await That(subject).Contains("d").And.Contains("e");
+
+				await That(Act).Throws<XunitException>()
+					.WithMessage("""
+					             Expected that subject
+					             contains "d" at least once and contains "e" at least once,
+					             but it did not contain it
+
+					             Collection:
+					             [
+					               "a",
+					               "b",
+					               "c"
+					             ]
+					             """);
+			}
 		}
 
 		public sealed class StringItemTests
diff --git a/Tests/aweXpect.Tests/Collections/ThatDictionary.ContainsKey.Tests.cs b/Tests/aweXpect.Tests/Collections/ThatDictionary.ContainsKey.Tests.cs
index 97fc3eeb6..2e797d26e 100644
--- a/Tests/aweXpect.Tests/Collections/ThatDictionary.ContainsKey.Tests.cs
+++ b/Tests/aweXpect.Tests/Collections/ThatDictionary.ContainsKey.Tests.cs
@@ -144,6 +144,33 @@ Expected that subject
 					             but it was <null>
 					             """);
 			}
+
+			[Fact]
+			public async Task WithMultipleFailures_ShouldIncludeCollectionOnlyOnce()
+			{
+				IDictionary<int, string> subject = ToDictionary([1, 2, 3,], ["foo", "bar", "baz",]);
+
+				async Task Act()
+					=> await That(subject).ContainsKey(4).And.ContainsKey(5);
+
+				await That(Act).Throws<XunitException>()
+					.WithMessage("""
+					             Expected that subject
+					             contains key 4 and contains key 5,
+					             but it contained only [
+					               1,
+					               2,
+					               3
+					             ]
+					             
+					             Dictionary:
+					             {
+					               [1] = "foo",
+					               [2] = "bar",
+					               [3] = "baz"
+					             }
+					             """);
+			}
 		}
 	}
 }
diff --git a/Tests/aweXpect.Tests/Collections/ThatEnumerable.Contains.EnumerableTests.cs b/Tests/aweXpect.Tests/Collections/ThatEnumerable.Contains.EnumerableTests.cs
index db72b3638..17a2a6aa3 100644
--- a/Tests/aweXpect.Tests/Collections/ThatEnumerable.Contains.EnumerableTests.cs
+++ b/Tests/aweXpect.Tests/Collections/ThatEnumerable.Contains.EnumerableTests.cs
@@ -373,6 +373,25 @@ Expected that subject
 					             but it was <null>
 					             """);
 			}
+
+			[Fact]
+			public async Task WithMultipleFailures_ShouldIncludeCollectionOnlyOnce()
+			{
+				IEnumerable subject = ToEnumerable([1, 2, 3,]);
+
+				async Task Act()
+					=> await That(subject).Contains(4).And.Contains(5);
+
+				await That(Act).Throws<XunitException>()
+					.WithMessage("""
+					             Expected that subject
+					             contains 4 at least once and contains 5 at least once,
+					             but it did not contain it
+
+					             Collection:
+					             [1, 2, 3]
+					             """);
+			}
 		}
 
 		public sealed class EnumerablePredicateTests
diff --git a/Tests/aweXpect.Tests/Collections/ThatEnumerable.Contains.ImmutableTests.cs b/Tests/aweXpect.Tests/Collections/ThatEnumerable.Contains.ImmutableTests.cs
index 6961cc443..4419a3d9d 100644
--- a/Tests/aweXpect.Tests/Collections/ThatEnumerable.Contains.ImmutableTests.cs
+++ b/Tests/aweXpect.Tests/Collections/ThatEnumerable.Contains.ImmutableTests.cs
@@ -372,6 +372,29 @@ but it did not contain it
 					              {Formatter.Format(subject)}
 					              """);
 			}
+
+			[Fact]
+			public async Task WithMultipleFailures_ShouldIncludeCollectionOnlyOnce()
+			{
+				ImmutableArray<string?> subject = ["a", "b", "c",];
+
+				async Task Act()
+					=> await That(subject).Contains("d").And.Contains("e");
+
+				await That(Act).Throws<XunitException>()
+					.WithMessage("""
+					             Expected that subject
+					             contains "d" at least once and contains "e" at least once,
+					             but it did not contain it
+
+					             Collection:
+					             [
+					               "a",
+					               "b",
+					               "c"
+					             ]
+					             """);
+			}
 		}
 
 		public sealed class ImmutableStringItemTests
diff --git a/Tests/aweXpect.Tests/Collections/ThatEnumerable.Contains.Tests.cs b/Tests/aweXpect.Tests/Collections/ThatEnumerable.Contains.Tests.cs
index 908a8259d..c554811d3 100644
--- a/Tests/aweXpect.Tests/Collections/ThatEnumerable.Contains.Tests.cs
+++ b/Tests/aweXpect.Tests/Collections/ThatEnumerable.Contains.Tests.cs
@@ -417,6 +417,29 @@ Expected that subject
 					             but it was <null>
 					             """);
 			}
+
+			[Fact]
+			public async Task WithMultipleFailures_ShouldIncludeCollectionOnlyOnce()
+			{
+				IEnumerable<string> subject = ToEnumerable(["a", "b", "c",]);
+
+				async Task Act()
+					=> await That(subject).Contains("d").And.Contains("e");
+
+				await That(Act).Throws<XunitException>()
+					.WithMessage("""
+					             Expected that subject
+					             contains "d" at least once and contains "e" at least once,
+					             but it did not contain it
+
+					             Collection:
+					             [
+					               "a",
+					               "b",
+					               "c"
+					             ]
+					             """);
+			}
 		}
 
 		public sealed class StringItemTests
diff --git a/Tests/aweXpect.Tests/Collections/ThatReadOnlyDictionary.ContainsKey.Tests.cs b/Tests/aweXpect.Tests/Collections/ThatReadOnlyDictionary.ContainsKey.Tests.cs
index e738615b6..35b32d5de 100644
--- a/Tests/aweXpect.Tests/Collections/ThatReadOnlyDictionary.ContainsKey.Tests.cs
+++ b/Tests/aweXpect.Tests/Collections/ThatReadOnlyDictionary.ContainsKey.Tests.cs
@@ -145,6 +145,33 @@ Expected that subject
 					             but it was <null>
 					             """);
 			}
+
+			[Fact]
+			public async Task WithMultipleFailures_ShouldIncludeCollectionOnlyOnce()
+			{
+				IReadOnlyDictionary<int, string> subject = ToDictionary([1, 2, 3,], ["foo", "bar", "baz",]);
+
+				async Task Act()
+					=> await That(subject).ContainsKey(4).And.ContainsKey(5);
+
+				await That(Act).Throws<XunitException>()
+					.WithMessage("""
+					             Expected that subject
+					             contains key 4 and contains key 5,
+					             but it contained only [
+					               1,
+					               2,
+					               3
+					             ]
+
+					             Dictionary:
+					             {
+					               [1] = "foo",
+					               [2] = "bar",
+					               [3] = "baz"
+					             }
+					             """);
+			}
 		}
 	}
 }