diff --git a/Coder.Test/Languages/GoGeneratedSourceCompilesTests.cs b/Coder.Test/Languages/GoGeneratedSourceCompilesTests.cs
index bbc4f74..4dc1831 100644
--- a/Coder.Test/Languages/GoGeneratedSourceCompilesTests.cs
+++ b/Coder.Test/Languages/GoGeneratedSourceCompilesTests.cs
@@ -176,6 +176,90 @@ public void ConditionalExpressions_InferParameterTypesAndLowerNestedReturns()
 		});
 	}
 
+	/// <summary>
+	/// Tests that a condition comparing against a struct literal compiles in every position a
+	/// conditional is lowered to an <c>if</c>, and is still what <c>gofmt</c> writes.
+	/// </summary>
+	/// <remarks>
+	/// Go reads <c>Pair{</c> in the header of an <c>if</c> as the start of the block, so the literal
+	/// has to be parenthesised once the clause's own parentheses are left off (issue #105).
+	/// </remarks>
+	[TestMethod]
+	public void ConditionComparingAgainstAStructLiteral_Compiles()
+	{
+		if (ToolchainHarness.FindOnPath("version", "go") is null)
+		{
+			Assert.Inconclusive("No Go toolchain on the path, so nothing was compiled.");
+			return;
+		}
+
+		SourceFile file = new("literals");
+		ClassDeclaration pair = new("Pair") { Kind = TypeDeclarationKind.Struct };
+		pair.Members.Add(new VariableDeclaration("x", "int"));
+		pair.Members.Add(new VariableDeclaration("y", "int"));
+		file.Members.Add(pair);
+
+		// The return the issue reproduced with, the struct on the right.
+		FunctionDeclaration returned = new("returned") { ReturnType = new TypeReference("int") };
+		returned.Parameters.Add(new Parameter("p", "Pair"));
+		returned.Body.Add(new ReturnStatement(new ConditionalExpression(
+			new BinaryExpression(new VariableReference("p"), BinaryOperator.Equal, PairLiteral()),
+			new LiteralExpression<int>(1),
+			new LiteralExpression<int>(0))));
+		file.Members.Add(returned);
+
+		// An assignment, the struct on the left and spelled with field names.
+		FunctionDeclaration assigned = new("assigned") { ReturnType = new TypeReference("int") };
+		assigned.Parameters.Add(new Parameter("p", "Pair"));
+		assigned.Body.Add(new VariableDeclaration("r", "int", new LiteralExpression<int>(0)));
+		ConstructionExpression named = new(new TypeReference("Pair"));
+		named.Arguments.Add(new MemberInitialiser("x") { Value = new LiteralExpression<int>(1) });
+		named.Arguments.Add(new MemberInitialiser("y") { Value = new LiteralExpression<int>(2) });
+		assigned.Body.Add(new AssignmentStatement(
+			new VariableReference("r"),
+			new ConditionalExpression(
+				new BinaryExpression(named, BinaryOperator.NotEqual, new VariableReference("p")),
+				new LiteralExpression<int>(1),
+				new LiteralExpression<int>(0))));
+		assigned.Body.Add(new ReturnStatement(new VariableReference("r")));
+		file.Members.Add(assigned);
+
+		// Inside another expression, where the conditional becomes a function literal called in place.
+		FunctionDeclaration nested = new("nested") { ReturnType = new TypeReference("int") };
+		nested.Parameters.Add(new Parameter("p", "Pair"));
+		nested.Body.Add(new ReturnStatement(new BinaryExpression(
+			new ConditionalExpression(
+				new BinaryExpression(new VariableReference("p"), BinaryOperator.Equal, PairLiteral()),
+				new LiteralExpression<int>(1),
+				new LiteralExpression<int>(0)),
+			BinaryOperator.Add,
+			new LiteralExpression<int>(1))));
+		file.Members.Add(nested);
+
+		string generated = new GoGenerator().Generate(file);
+		Assert.Contains("p == (Pair{1, 2})", generated, StringComparison.Ordinal, generated);
+
+		ToolchainHarness.InTemporaryDirectory(directory =>
+		{
+			File.WriteAllText(Path.Combine(directory, "go.mod"), Module);
+			File.WriteAllText(Path.Combine(directory, "literals.go"), generated);
+			(int exitCode, string output) = ToolchainHarness.Run("go", "build ./...", directory);
+			Assert.AreEqual(0, exitCode, $"Go rejected the generated source:{Environment.NewLine}{output}{Environment.NewLine}{generated}");
+
+			(int formatted, string differs) = ToolchainHarness.Run("gofmt", "-l literals.go", directory);
+			Assert.AreEqual(0, formatted, $"gofmt did not run:{Environment.NewLine}{differs}");
+			Assert.AreEqual(string.Empty, differs.Trim(), "gofmt would rewrite the generated source.");
+		});
+
+		static ConstructionExpression PairLiteral()
+		{
+			ConstructionExpression literal = new(new TypeReference("Pair"));
+			literal.Arguments.Add(new LiteralExpression<int>(1));
+			literal.Arguments.Add(new LiteralExpression<int>(2));
+			return literal;
+		}
+	}
+
 	/// <summary>
 	/// Tests that the arguments an entry point is handed are the ones the user typed, without the
 	/// program's own path that Go puts first — which is what they are in every other target.
diff --git a/Coder/Languages/GoGenerator.cs b/Coder/Languages/GoGenerator.cs
index 18c6a95..01353d7 100644
--- a/Coder/Languages/GoGenerator.cs
+++ b/Coder/Languages/GoGenerator.cs
@@ -1638,20 +1638,26 @@ private void WriteChoice(
 	/// Only the outermost pair: <c>gofmt</c> takes no view on the ones inside, which are what make
 	/// the expression unambiguous in the first place.
 	/// </para>
+	/// <para>
+	/// Taking that pair off exposes the operands to the clause, and a struct literal is the one operand
+	/// that cannot stand there: Go reads <c>Point{</c> in the header of an <c>if</c> as the start of
+	/// the block, so <c>if p == Point{1, 2} {</c> is a syntax error. The language's own answer is to
+	/// parenthesise the literal, which <c>gofmt</c> keeps, so <see cref="WriteConditionOperand"/> does.
+	/// </para>
 	/// </remarks>
 	private void WriteCondition(AstNode condition, CodeBlocker code)
 	{
 		switch (condition)
 		{
 			case BinaryExpression binary:
-				GenerateInternal(binary.Left, code);
+				WriteConditionOperand(binary.Left, code);
 				code.Write($" {GetOperatorSpelling(binary.Operator)} ");
-				GenerateInternal(binary.Right, code);
+				WriteConditionOperand(binary.Right, code);
 				return;
 
 			case UnaryExpression unary:
 				code.Write(GetUnaryOperatorSpelling(unary.Operator));
-				GenerateInternal(unary.Operand, code);
+				WriteConditionOperand(unary.Operand, code);
 				return;
 
 			default:
@@ -1660,6 +1666,25 @@ private void WriteCondition(AstNode condition, CodeBlocker code)
 		}
 	}
 
+	/// <summary>
+	/// Writes one operand of the expression an <c>if</c> tests, parenthesising a struct literal so the
+	/// clause does not end at its opening brace.
+	/// </summary>
+	/// <param name="operand">The operand to write.</param>
+	/// <param name="code">The writer to emit into.</param>
+	private void WriteConditionOperand(AstNode operand, CodeBlocker code)
+	{
+		if (operand is ConstructionExpression construction && IsCompositeLiteral(construction))
+		{
+			code.Write("(");
+			GenerateInternal(operand, code);
+			code.Write(")");
+			return;
+		}
+
+		GenerateInternal(operand, code);
+	}
+
 	/// <inheritdoc/>
 	/// <remarks>
 	/// Where the statement around it could not take the lowering — nested inside another expression,
@@ -1720,7 +1745,7 @@ protected override void GenerateConstructionExpression(ConstructionExpression co
 
 		string type = SpellType(construction.Type);
 
-		if (construction.Arguments.Count != 1 || construction.Arguments.Any(argument => argument is MemberInitialiser))
+		if (IsCompositeLiteral(construction))
 		{
 			code.Write(type);
 			WriteElementList(construction, code, "{", "}", "{}");
@@ -1732,6 +1757,17 @@ protected override void GenerateConstructionExpression(ConstructionExpression co
 		code.Write(")");
 	}
 
+	/// <summary>
+	/// Reports whether <see cref="GenerateConstructionExpression"/> writes a construction as a
+	/// composite literal in braces rather than as a conversion in parentheses.
+	/// </summary>
+	/// <param name="construction">The construction to classify.</param>
+	/// <returns>True when it is written with braces.</returns>
+	private static bool IsCompositeLiteral(ConstructionExpression construction) =>
+		construction.Type is null
+		|| construction.Arguments.Count != 1
+		|| construction.Arguments.Any(argument => argument is MemberInitialiser);
+
 	/// <inheritdoc/>
 	/// <remarks>
 	/// Go's <c>main</c> takes no arguments and returns nothing, so a program that wants either