condtional multi-unwrap and guard clauses

LANGUAGE.md

@@ -25,7 +25,7 @@
 - information-preserving and information-forgetting pointer-to-array decay and sentinel slice/pointer weakening; array values never implicitly decay
 - narrow immutable zero-terminated byte pointer conversion to `*c_char` and `[*;0]c_char`, without general `u8`/`c_char` interchange
 - optionals with trapping postfix `?`, `orelse`, and nullable pointer representation
-- conditional optional unwrapping with immutable then-block bindings: `if value |binding| { ... }`
+- conditional optional unwrapping with immutable guard/then-block bindings, guarded captures, and left-to-right short-circuiting multi-unwrap: `if first and second |a, b : guard| { ... }`
 - source-order native structs, defined or opaque `c_struct`, and keyed record literals
 - complete plain imported C structs and unions as runtime values; incomplete or unsupported-layout records remain pointer-only
 - C function pointer types as pointer-sized runtime values, including manual `*c_func(...) T` spelling and nullable imported callback typedefs

TODO.md

@@ -80,7 +80,7 @@
     - function-like macros and non-literal macro expressions remain unsupported
   - static inline functions (implemented)
 
-5. control flow
+5. control flow (implemented)
   - boolean expressions (implemented)
     - `bool` type with `true` / `false` literals
     - comparison operators: `==`, `!=`, `<`, `<=`, `>`, `>=` (numeric operands widen; `bool` supports only `==` / `!=`)
@@ -93,8 +93,8 @@
     - single immutable binding scoped to the then-block; `v` not visible in `else` or after the `if`
     - `|` lexes as a new `Pipe` token; the `.If` reuses AST `name` / HIR `local` to carry the binding (no new statement kind)
     - new `Optional_Is_Some` / `Optional_Value` IR opcodes (the `Unwrap` presence-test + extract, minus the trap)
-  - conditional unwrapping with guard clause:  `if val |v : v >= 10| { ... } else { ... }` - unwrap `val` into `v` if it is not `none`
+  - conditional unwrapping with guard clause (implemented):  `if val |v : v >= 10| { ... } else { ... }` - enter the then-block when `val` is not `none` and the guard is true
-  - multi-unwrap (see section below)
+  - multi-unwrap (implemented; see section below)
   - while loops (implemented; operates on boolean conditions). examples:
     - `while condition { ... }` - iterate while the condition is true
     - `while condition : i = i + 1 { ... }` - execute the update after each completed iteration

compiler/ast/ast.odin

@@ -136,14 +136,18 @@ Stmt :: struct {
 	pointer_capture: bool,
 	target:     Expr_Id,
 	expr:       Expr_Id,
-	// `If` statements use `expr` as the condition, `body` as the then-block, and
+	// `If` statements use `expr` as the condition, `captures` as optional
-	// `else_body` as the else-block. An `else if` chain is represented as an
+	// unwrap binding names, `guard` as the optional post-unwrap boolean
-	// `else_body` holding a single nested `If` statement.
+	// condition, `body` as the then-block, and `else_body` as the else-block.
+	// An `else if` chain is represented as an `else_body` holding a single
+	// nested `If` statement.
 	// `While` statements use `expr` as the condition, `body` as the loop body,
 	// and `update` as the optional post-iteration statement.
 	// `For` statements use `expr` as the iterable, `name` as the item capture,
 	// `index_name` as the optional index capture, and `pointer_capture` to
 	// distinguish `|@item|` from copy capture.
+	captures:   []symbol.Id,
+	guard:      Expr_Id,
 	body:       []Stmt_Id,
 	else_body:  []Stmt_Id,
 	update:     Stmt_Id,
@@ -263,6 +267,7 @@ destroy_module :: proc(module: ^Module) {
 		delete(expr.args, module.allocator)
 	}
 	for statement in module.statements {
+		delete(statement.captures, module.allocator)
 		delete(statement.body, module.allocator)
 		delete(statement.else_body, module.allocator)
 	}

compiler/checker/checker.odin

@@ -629,6 +629,9 @@ mark_block_imports_used :: proc(checker: ^Checker, statements: []ast.Stmt_Id, fi
 			}
 		case .If:
 			mark_expr_imports_used(checker, statement.expr, file)
+			if statement.guard != ast.INVALID_EXPR {
+				mark_expr_imports_used(checker, statement.guard, file)
+			}
 			mark_block_imports_used(checker, statement.body, file)
 			mark_block_imports_used(checker, statement.else_body, file)
 		case .While:
@@ -1403,6 +1406,24 @@ infer_expr :: proc(
 	return last
 }
 
+flatten_conditional_unwrap_operands :: proc(
+	module: ^ast.Module,
+	expr_id: ast.Expr_Id,
+	operands: ^[dynamic]ast.Expr_Id,
+) {
+	if expr_id == ast.INVALID_EXPR || int(expr_id) >= len(module.exprs) {
+		append(operands, expr_id)
+		return
+	}
+	expr := module.exprs[expr_id]
+	if expr.kind == .And {
+		flatten_conditional_unwrap_operands(module, expr.left, operands)
+		flatten_conditional_unwrap_operands(module, expr.right, operands)
+		return
+	}
+	append(operands, expr_id)
+}
+
 infer_statements :: proc(
 	checker: ^Checker,
 	statements: []ast.Stmt_Id,
@@ -1438,16 +1459,36 @@ infer_statements :: proc(
 				}
 			}
 		case .If:
-			value_type := infer_expr(checker, statement.expr, locals^[:], pkg, file, demanded)
+			if len(statement.captures) > 0 {
-			if statement.name != symbol.INVALID {
+				operands: [dynamic]ast.Expr_Id
-				// Conditional unwrap: `v` is in scope (with the unwrapped type) only inside the then-block.
+				operands.allocator = checker.allocator
-				child := types.child_type(value_type, &checker.module.types) if types.is_optional(value_type, &checker.module.types) else types.INVALID
+				flatten_conditional_unwrap_operands(checker.ast_module, statement.expr, &operands)
-				binding_start := len(locals^)
+				operand_types := make([]types.Type, len(operands), checker.allocator)
-				append(locals, Infer_Local{name = statement.name, type = child})
+				for operand, index in operands {
+					operand_types[index] = infer_expr(checker, operand, locals^[:], pkg, file, demanded)
+				}
+				capture_start := len(locals^)
+				for capture, index in statement.captures {
+					if capture == checker.sink_symbol {
+						continue
+					}
+					capture_type := types.INVALID
+					if index < len(operand_types) &&
+					   types.is_optional(operand_types[index], &checker.module.types) {
+						capture_type = types.child_type(operand_types[index], &checker.module.types)
+					}
+					append(locals, Infer_Local{name=capture, type=capture_type})
+				}
+				if statement.guard != ast.INVALID_EXPR {
+					_ = infer_expr(checker, statement.guard, locals^[:], pkg, file, demanded)
+				}
 				infer_statements(checker, statement.body, locals, pkg, file, demanded, result)
-				resize(locals, binding_start)
+				resize(locals, capture_start)
 				infer_statements(checker, statement.else_body, locals, pkg, file, demanded, result)
+				delete(operand_types, checker.allocator)
+				delete(operands)
 			} else {
+				_ = infer_expr(checker, statement.expr, locals^[:], pkg, file, demanded)
 				infer_statements(checker, statement.body, locals, pkg, file, demanded, result)
 				infer_statements(checker, statement.else_body, locals, pkg, file, demanded, result)
 			}
@@ -3142,37 +3183,135 @@ build_block :: proc(
 				})
 			}
 		case .If:
-			if statement.name != symbol.INVALID {
+			if len(statement.captures) > 0 {
-				// Conditional unwrap `if opt |v| { ... }`: `expr` is the optional, `v`
+				ast_operands: [dynamic]ast.Expr_Id
-				// binds the unwrapped value (immutable) for the duration of the then-block.
+				ast_operands.allocator = checker.allocator
-				value := build_expr(checker, statement.expr, ctx.locals^[:], ctx.global_reads, ctx.calls, types.INVALID, ctx.pkg, ctx.file)
+				flatten_conditional_unwrap_operands(checker.ast_module, statement.expr, &ast_operands)
-				value_type := checker.module.exprs[value].type
+
-				child := types.INVALID
+				valid_unwrap := true
-				if checker.module.exprs[value].kind != .Invalid && !types.is_optional(value_type, &checker.module.types) {
+				diagnostic := source.INVALID_DIAGNOSTIC
-					id := source.add(checker.diagnostics, statement.span, "'if' unwrap requires an optional value")
+				if len(ast_operands) != len(statement.captures) {
-					value = invalid_hir_expr(checker, statement.span, id)
+					diagnostic = source.addf(
-					ctx.problematic^ = true
+						checker.diagnostics,
-				} else if checker.module.exprs[value].kind != .Invalid {
+						statement.span,
-					child = types.child_type(value_type, &checker.module.types)
+						"'if' unwrap has %d operands but %d captures",
+						len(ast_operands),
+						len(statement.captures),
+					)
+					valid_unwrap = false
 				}
-				binding := hir.local_id(len(ctx.hir_locals^))
+
-				append(ctx.hir_locals, hir.Local{name = statement.name, type = child, mutable = false})
+				values := make([]hir.Expr_Id, len(ast_operands), checker.allocator)
-				locals_before := len(ctx.locals^)
+				child_types := make([]types.Type, len(ast_operands), checker.allocator)
-				append(ctx.locals, Build_Local{name = statement.name, type = child, mutable = false, id = binding})
+				for operand, index in ast_operands {
-				then_body := build_block(ctx, statement.body)
+					child_types[index] = types.INVALID
-				resize(ctx.locals, locals_before)
+					value := build_expr(
+						checker, operand, ctx.locals^[:], ctx.global_reads, ctx.calls,
+						types.INVALID, ctx.pkg, ctx.file,
+					)
+					values[index] = value
+					value_type := checker.module.exprs[value].type
+					if checker.module.exprs[value].kind == .Invalid {
+						valid_unwrap = false
+						if diagnostic == source.INVALID_DIAGNOSTIC {
+							diagnostic = checker.module.exprs[value].diagnostic
+						}
+					} else if !types.is_optional(value_type, &checker.module.types) {
+						diagnostic = source.addf(
+							checker.diagnostics,
+							checker.ast_module.exprs[operand].span,
+							"'if' unwrap requires an optional value (operand %d)",
+							index + 1,
+						)
+						valid_unwrap = false
+					} else {
+						child_types[index] = types.child_type(value_type, &checker.module.types)
+					}
+				}
+
+				capture_start := len(ctx.locals^)
+				unwraps: [dynamic]hir.Conditional_Unwrap
+				unwraps.allocator = checker.allocator
+				for capture, index in statement.captures {
+					child := child_types[index] if index < len(child_types) else types.INVALID
+					local := hir.INVALID_LOCAL
+					if capture != checker.sink_symbol {
+						if _, duplicate := find_build_local(ctx.locals^[capture_start:], capture); duplicate {
+							diagnostic = source.add(
+								checker.diagnostics,
+								statement.span,
+								"'if' unwrap captures must have distinct names",
+							)
+							valid_unwrap = false
+						}
+						local = hir.local_id(len(ctx.hir_locals^))
+						append(ctx.hir_locals, hir.Local{name=capture, type=child, mutable=false})
+						append(ctx.locals, Build_Local{name=capture, type=child, mutable=false, id=local})
+					}
+					if index < len(values) {
+						append(&unwraps, hir.Conditional_Unwrap{expr=values[index], local=local})
+					}
+				}
+
+				guard := hir.INVALID_EXPR
+				if statement.guard != ast.INVALID_EXPR {
+					guard = build_expr(
+						checker, statement.guard, ctx.locals^[:], ctx.global_reads, ctx.calls,
+						types.BOOL, ctx.pkg, ctx.file,
+					)
+					if checker.module.exprs[guard].kind == .Invalid {
+						valid_unwrap = false
+						if diagnostic == source.INVALID_DIAGNOSTIC {
+							diagnostic = checker.module.exprs[guard].diagnostic
+						}
+					} else if !types.is_bool(checker.module.exprs[guard].type) {
+						diagnostic = source.add(
+							checker.diagnostics,
+							checker.ast_module.exprs[statement.guard].span,
+							"'if' unwrap guard must be a bool",
+						)
+						valid_unwrap = false
+					}
+				}
+
+				then_body := build_block(ctx, statement.body, capture_start)
+				resize(ctx.locals, capture_start)
 				else_body: []hir.Stmt_Id = nil
 				if statement.else_body != nil {
 					else_body = build_block(ctx, statement.else_body)
 				}
 				append(&body, hir.stmt_id(len(checker.module.statements)))
+				if valid_unwrap {
 					append(&checker.module.statements, hir.Stmt{
-					kind = .If, span = statement.span, expr = value,
+						kind=.If,
-					then_body = then_body, else_body = else_body,
+						span=statement.span,
-					local = binding, target = hir.INVALID_EXPR,
+						expr=hir.INVALID_EXPR,
-					diagnostic = source.INVALID_DIAGNOSTIC,
+						unwraps=unwraps[:],
+						guard=guard,
+						then_body=then_body,
+						else_body=else_body,
+						local=hir.INVALID_LOCAL,
+						target=hir.INVALID_EXPR,
+						diagnostic=source.INVALID_DIAGNOSTIC,
 					})
-				ctx.problematic^ = ctx.problematic^ || checker.module.exprs[value].kind == .Invalid
+				} else {
+					delete(unwraps)
+					delete(then_body, checker.allocator)
+					delete(else_body, checker.allocator)
+					append(&checker.module.statements, hir.Stmt{
+						kind=.Trap,
+						span=statement.span,
+						expr=hir.INVALID_EXPR,
+						guard=hir.INVALID_EXPR,
+						local=hir.INVALID_LOCAL,
+						target=hir.INVALID_EXPR,
+						diagnostic=diagnostic,
+					})
+					ctx.problematic^ = true
+				}
+				delete(values, checker.allocator)
+				delete(child_types, checker.allocator)
+				delete(ast_operands)
 				continue
 			}
 			condition := build_expr(checker, statement.expr, ctx.locals^[:], ctx.global_reads, ctx.calls, types.BOOL, ctx.pkg, ctx.file)
@@ -3189,6 +3328,7 @@ build_block :: proc(
 			append(&body, hir.stmt_id(len(checker.module.statements)))
 			append(&checker.module.statements, hir.Stmt{
 				kind = .If, span = statement.span, expr = condition,
+				guard = hir.INVALID_EXPR,
 				then_body = then_body, else_body = else_body,
 				local = hir.INVALID_LOCAL, target = hir.INVALID_EXPR,
 				diagnostic = source.INVALID_DIAGNOSTIC,

compiler/hir/hir.odin

@@ -134,6 +134,11 @@ Local :: struct {
 	parameter: bool,
 }
 
+Conditional_Unwrap :: struct {
+	expr:  Expr_Id,
+	local: Local_Id,
+}
+
 Stmt_Kind :: enum u8 {
 	Declaration,
 	Assignment,
@@ -155,13 +160,17 @@ Stmt :: struct {
 	expr:       Expr_Id,
 	iterator_type: types.Type,
 	pointer_capture: bool,
-	// `If` statements use `expr` as the condition and `then_body`/`else_body` as
+	// Boolean `If` statements use `expr` as the condition. Conditional unwraps
-	// the branch statement lists.
+	// use `unwraps` for the ordered optional expressions and capture locals, and
+	// `guard` for the optional boolean checked after every unwrap succeeds.
+	// Both forms use `then_body`/`else_body` as the branch statement lists.
 	// `While` statements use `expr` as the condition, `then_body` as the loop
 	// body, and `update` as the optional post-iteration statement.
 	// `For` statements use `expr` as the iterable, `local` as the item capture,
 	// `index_local` as the optional sequence index, and `iterator_type` as the
 	// normalized many-item pointer type for sequence iteration.
+	unwraps:    []Conditional_Unwrap,
+	guard:      Expr_Id,
 	then_body:  []Stmt_Id,
 	else_body:  []Stmt_Id,
 	update:     Stmt_Id,
@@ -232,6 +241,7 @@ destroy_module :: proc(module: ^Module) {
 		delete(expr.args, module.allocator)
 	}
 	for statement in module.statements {
+		delete(statement.unwraps, module.allocator)
 		delete(statement.then_body, module.allocator)
 		delete(statement.else_body, module.allocator)
 	}

compiler/lower/lower.odin

@@ -669,57 +669,117 @@ lower_statements :: proc(state: ^State, statements: []hir.Stmt_Id) {
 				diagnostic=statement.diagnostic,
 			})
 		case .If:
-			// A conditional unwrap (`if opt |v| { ... }`) carries the binding local id in
-			// `statement.local`; `expr` is then the optional, not a bool condition. Test it
-			// for presence, and inside the then-block bind the unwrapped value to the local.
-			is_unwrap := statement.local != hir.INVALID_LOCAL
-			opt := ir.INVALID_INSTRUCTION
-			cond: ir.Instruction_Id
-			if is_unwrap {
-				opt = lower_expr(state, statement.expr)
-				cond = append_instruction(state, ir.Instruction{
-					op=.Optional_Is_Some, span=statement.span, type=types.BOOL,
-					target=ir.INVALID_REF, a=opt, b=ir.INVALID_INSTRUCTION,
-					diagnostic=source.INVALID_DIAGNOSTIC,
-				})
-			} else {
-				cond = lower_expr(state, statement.expr)
-			}
 			has_else := statement.else_body != nil
 			then_lbl := fresh_label(state)
 			else_lbl := fresh_label(state) if has_else else then_lbl
 			merge_lbl := fresh_label(state)
 			false_target := else_lbl if has_else else merge_lbl
+
+			if len(statement.unwraps) > 0 {
+				// Evaluate each optional exactly once, entering the next operand only
+				// after the previous one is present. Capture storage is initialized in
+				// these success blocks so the optional guard can use every binding.
+				for unwrap in statement.unwraps {
+					optional := lower_expr(state, unwrap.expr)
+					present := append_instruction(state, ir.Instruction{
+						op=.Optional_Is_Some,
+						span=statement.span,
+						type=types.BOOL,
+						target=ir.INVALID_REF,
+						a=optional,
+						b=ir.INVALID_INSTRUCTION,
+						diagnostic=source.INVALID_DIAGNOSTIC,
+					})
+					success_lbl := fresh_label(state)
+					append_instruction(state, ir.Instruction{
+						op=.Cond_Br,
+						span=statement.span,
+						type=types.VOID,
+						a=present,
+						integer=success_lbl,
+						target=ir.Ref(u32(false_target)),
+						b=ir.INVALID_INSTRUCTION,
+						diagnostic=source.INVALID_DIAGNOSTIC,
+					})
+					append_instruction(state, ir.Instruction{
+						op=.Label,
+						span=statement.span,
+						type=types.VOID,
+						integer=success_lbl,
+						target=ir.INVALID_REF,
+						a=ir.INVALID_INSTRUCTION,
+						b=ir.INVALID_INSTRUCTION,
+						diagnostic=source.INVALID_DIAGNOSTIC,
+					})
+					if unwrap.local != hir.INVALID_LOCAL && int(unwrap.local) < len(state.func_locals) {
+						local := state.func_locals[unwrap.local]
+						slot := append_instruction(state, ir.Instruction{
+							op=.Alloca,
+							span=statement.span,
+							type=local.type,
+							target=ir.local_ref(ir.Local_Id(unwrap.local)),
+							a=ir.INVALID_INSTRUCTION,
+							b=ir.INVALID_INSTRUCTION,
+							diagnostic=source.INVALID_DIAGNOSTIC,
+						})
+						state.local_slots[unwrap.local] = slot
+						inner := append_instruction(state, ir.Instruction{
+							op=.Optional_Value,
+							span=statement.span,
+							type=local.type,
+							target=ir.INVALID_REF,
+							a=optional,
+							b=ir.INVALID_INSTRUCTION,
+							diagnostic=source.INVALID_DIAGNOSTIC,
+						})
+						append_instruction(state, ir.Instruction{
+							op=.Store,
+							span=statement.span,
+							type=local.type,
+							target=ir.INVALID_REF,
+							a=slot,
+							b=inner,
+							diagnostic=source.INVALID_DIAGNOSTIC,
+						})
+					}
+				}
+				if statement.guard != hir.INVALID_EXPR {
+					guard := lower_expr(state, statement.guard)
+					append_instruction(state, ir.Instruction{
+						op=.Cond_Br,
+						span=statement.span,
+						type=types.VOID,
+						a=guard,
+						integer=then_lbl,
+						target=ir.Ref(u32(false_target)),
+						b=ir.INVALID_INSTRUCTION,
+						diagnostic=source.INVALID_DIAGNOSTIC,
+					})
+				} else {
+					append_instruction(state, ir.Instruction{
+						op=.Br,
+						span=statement.span,
+						type=types.VOID,
+						integer=then_lbl,
+						target=ir.INVALID_REF,
+						a=ir.INVALID_INSTRUCTION,
+						b=ir.INVALID_INSTRUCTION,
+						diagnostic=source.INVALID_DIAGNOSTIC,
+					})
+				}
+			} else {
+				cond := lower_expr(state, statement.expr)
 				append_instruction(state, ir.Instruction{
 					op=.Cond_Br, span=statement.span, type=types.VOID,
 					a=cond, integer=then_lbl, target=ir.Ref(u32(false_target)),
 					b=ir.INVALID_INSTRUCTION, diagnostic=source.INVALID_DIAGNOSTIC,
 				})
+			}
 			append_instruction(state, ir.Instruction{
 				op=.Label, span=statement.span, type=types.VOID, integer=then_lbl,
 				target=ir.INVALID_REF, a=ir.INVALID_INSTRUCTION, b=ir.INVALID_INSTRUCTION,
 				diagnostic=source.INVALID_DIAGNOSTIC,
 			})
-			if is_unwrap && int(statement.local) < len(state.func_locals) {
-				local := state.func_locals[statement.local]
-				slot := append_instruction(state, ir.Instruction{
-					op=.Alloca, span=statement.span, type=local.type,
-					target=ir.local_ref(ir.Local_Id(statement.local)),
-					a=ir.INVALID_INSTRUCTION, b=ir.INVALID_INSTRUCTION,
-					diagnostic=source.INVALID_DIAGNOSTIC,
-				})
-				state.local_slots[statement.local] = slot
-				inner := append_instruction(state, ir.Instruction{
-					op=.Optional_Value, span=statement.span, type=local.type,
-					target=ir.INVALID_REF, a=opt, b=ir.INVALID_INSTRUCTION,
-					diagnostic=source.INVALID_DIAGNOSTIC,
-				})
-				append_instruction(state, ir.Instruction{
-					op=.Store, span=statement.span, type=local.type,
-					target=ir.INVALID_REF, a=slot, b=inner,
-					diagnostic=source.INVALID_DIAGNOSTIC,
-				})
-			}
 			lower_statements(state, statement.then_body)
 			append_instruction(state, ir.Instruction{
 				op=.Br, span=statement.span, type=types.VOID, integer=merge_lbl,

compiler/parser/parser.odin

@@ -1129,16 +1129,39 @@ parse_if :: proc(parser: ^Parser) -> ast.Stmt_Id {
 	parser.no_struct_literal = true
 	condition := parse_expression(parser)
 	parser.no_struct_literal = saved
-	binding := symbol.INVALID
+	captures: [dynamic]symbol.Id
+	captures.allocator = parser.module.allocator
+	guard := ast.INVALID_EXPR
 	if _, ok := allow(parser, .Pipe); ok {
-		name_tok, name_ok := allow(parser, .Identifier)
+		for {
-		if name_ok {
+			name_tok := current(parser)
-			binding = name_tok.symbol
+			if name_tok.kind == .Identifier || name_tok.kind == .Underscore {
+				advance(parser)
+				append(&captures, name_tok.symbol)
 			} else {
-			source.add(parser.diagnostics, current(parser).span, "expected a binding name after '|'")
+				source.add(parser.diagnostics, current(parser).span, "expected an unwrap capture name")
+				break
+			}
+			if _, comma_ok := allow(parser, .Comma); !comma_ok {
+				break
+			}
+			if current(parser).kind == .Colon || current(parser).kind == .Pipe {
+				source.add(parser.diagnostics, current(parser).span, "expected an unwrap capture after ','")
+				break
+			}
+		}
+		if _, guard_ok := allow(parser, .Colon); guard_ok {
+			if current(parser).kind == .Pipe {
+				source.add(parser.diagnostics, current(parser).span, "expected a guard expression after ':'")
+			} else {
+				saved = parser.no_struct_literal
+				parser.no_struct_literal = true
+				guard = parse_expression(parser)
+				parser.no_struct_literal = saved
+			}
 		}
 		if _, close_ok := allow(parser, .Pipe); !close_ok {
-			source.add(parser.diagnostics, current(parser).span, "expected '|' to close the unwrap binding")
+			source.add(parser.diagnostics, current(parser).span, "expected '|' to close unwrap captures")
 		}
 	}
 	skip_newlines(parser)
@@ -1164,8 +1187,9 @@ parse_if :: proc(parser: ^Parser) -> ast.Stmt_Id {
 	append(&parser.module.statements, ast.Stmt{
 		kind=.If,
 		span=span_from(start.span, previous(parser).span),
-		name=binding,
 		expr=condition,
+		captures=captures[:],
+		guard=guard,
 		body=then_body,
 		else_body=else_body,
 		diagnostic=source.INVALID_DIAGNOSTIC,

compiler_tests.odin

@@ -3823,11 +3823,121 @@ conditional_unwrap_compiles_and_runs :: proc(t: ^testing.T) {
 	status := compiler_core.compile_package("examples/programs/conditional_unwrap", output)
 	testing.expect_value(t, status, 0)
 	state := run_executable(output)
-	// present scalar binds and unwraps (40), none takes the else (+2), a present
+	// Single unwrap, guarded two/three-value unwraps, optional pointers, false
-	// optional pointer binds and derefs (+0), a none optional pointer is skipped.
+	// guards, and failed short-circuit chains preserve the expected total.
 	testing.expect_value(t, state.exit_code, 42)
 }
 
+@(test)
+conditional_unwrap_parser_captures_guard_and_parenthesized_chain :: proc(t: ^testing.T) {
+	text := `main :: func() void {
+	first ?i32 = 1
+	second ?i32 = 2
+	if (first and second) |a, b : a == 1 and b == 2| {
+		_ = a
+		_ = b
+	}
+}
+`
+	source_file := source.Source{path="test.bro", text=text}
+	diagnostics := source.init_diagnostics(&source_file)
+	defer source.destroy_diagnostics(&diagnostics)
+	symbols := symbol.init_table()
+	defer symbol.destroy_table(&symbols)
+	stream := lexer.lex(&source_file, &diagnostics, &symbols)
+	defer delete(stream.items)
+	module := parser.parse(&stream, &source_file, &diagnostics)
+	defer ast.destroy_module(&module)
+
+	testing.expect_value(t, len(diagnostics.items), 0)
+	statement := module.statements[module.functions[0].body[2]]
+	testing.expect_value(t, statement.kind, ast.Stmt_Kind.If)
+	testing.expect_value(t, len(statement.captures), 2)
+	testing.expect_value(t, module.exprs[statement.expr].kind, ast.Expr_Kind.And)
+	testing.expect(t, module.exprs[statement.expr].parenthesized)
+	testing.expect(t, statement.guard != ast.INVALID_EXPR)
+	testing.expect_value(t, module.exprs[statement.guard].kind, ast.Expr_Kind.And)
+}
+
+@(test)
+conditional_unwrap_allows_sink_captures :: proc(t: ^testing.T) {
+	text := `main :: func() void {
+	first ?i32 = 1
+	second ?i32 = 2
+	if first and second |_, value : value == 2| {
+		_ = value
+	}
+	if first |_| {}
+}
+`
+	source_file := source.Source{path="test.bro", text=text}
+	diagnostics := source.init_diagnostics(&source_file)
+	defer source.destroy_diagnostics(&diagnostics)
+	symbols := symbol.init_table()
+	defer symbol.destroy_table(&symbols)
+	stream := lexer.lex(&source_file, &diagnostics, &symbols)
+	defer delete(stream.items)
+	ast_module := parser.parse(&stream, &source_file, &diagnostics)
+	defer ast.destroy_module(&ast_module)
+	hir_module := checker.check(&ast_module, &diagnostics, &symbols)
+	defer hir.destroy_module(&hir_module)
+
+	testing.expect_value(t, len(diagnostics.items), 0)
+	main := hir_module.functions[0]
+	first_if := hir_module.statements[main.body[2]]
+	second_if := hir_module.statements[main.body[3]]
+	testing.expect_value(t, first_if.unwraps[0].local, hir.INVALID_LOCAL)
+	testing.expect(t, first_if.unwraps[1].local != hir.INVALID_LOCAL)
+	testing.expect_value(t, second_if.unwraps[0].local, hir.INVALID_LOCAL)
+}
+
+@(test)
+parser_diagnoses_malformed_conditional_unwrap_captures_and_guards :: proc(t: ^testing.T) {
+	cases := [4]struct {
+		text:   string,
+		needle: string,
+	}{
+		{`main :: func() void {
+	value ?i32 = 1
+	if value || {}
+}
+`, "expected an unwrap capture name"},
+		{`main :: func() void {
+	value ?i32 = 1
+	if value |capture,| {}
+}
+`, "expected an unwrap capture after ','"},
+		{`main :: func() void {
+	value ?i32 = 1
+	if value |capture :| {}
+}
+`, "expected a guard expression after ':'"},
+		{`main :: func() void {
+	value ?i32 = 1
+	if value |capture {}
+}
+`, "expected '|' to close unwrap captures"},
+	}
+	for test_case in cases {
+		source_file := source.Source{path="test.bro", text=test_case.text}
+		diagnostics := source.init_diagnostics(&source_file)
+		symbols := symbol.init_table()
+		stream := lexer.lex(&source_file, &diagnostics, &symbols)
+		module := parser.parse(&stream, &source_file, &diagnostics)
+
+		found := false
+		for diagnostic in diagnostics.items {
+			found = found || strings.contains(diagnostic.message, test_case.needle)
+		}
+		testing.expect(t, found)
+
+		ast.destroy_module(&module)
+		delete(stream.items)
+		symbol.destroy_table(&symbols)
+		source.destroy_diagnostics(&diagnostics)
+	}
+}
+
 @(test)
 if_unwrap_on_non_optional_is_diagnosed :: proc(t: ^testing.T) {
 	text := `main :: func() i32 {
@@ -3857,6 +3967,75 @@ if_unwrap_on_non_optional_is_diagnosed :: proc(t: ^testing.T) {
 	testing.expect(t, found)
 }
 
+@(test)
+conditional_unwrap_diagnostics_cover_counts_guards_and_capture_scope :: proc(t: ^testing.T) {
+	text := `main :: func() void {
+	first ?i32 = 1
+	second ?i32 = 2
+	plain i32 = 3
+
+	if first and second |one| {}
+	if first |one, two| {}
+	if first and second |same, same| {}
+	if plain |value| {}
+	if first |value : value| {}
+	if first and earlier |earlier, later| {}
+
+	if first |value| {
+		value = 2
+	}
+	if first |value| {
+		value i32 = 2
+		_ = value
+	}
+	if first |value| {
+		_ = value
+	} else {
+		_ = value
+	}
+	_ = value
+}
+`
+	source_file := source.Source{path="test.bro", text=text}
+	diagnostics := source.init_diagnostics(&source_file)
+	defer source.destroy_diagnostics(&diagnostics)
+	symbols := symbol.init_table()
+	defer symbol.destroy_table(&symbols)
+	stream := lexer.lex(&source_file, &diagnostics, &symbols)
+	defer delete(stream.items)
+	ast_module := parser.parse(&stream, &source_file, &diagnostics)
+	defer ast.destroy_module(&ast_module)
+	hir_module := checker.check(&ast_module, &diagnostics, &symbols)
+	defer hir.destroy_module(&hir_module)
+
+	count_mismatches := 0
+	duplicate := false
+	non_optional := false
+	guard := false
+	outer_operand_scope := false
+	immutable := false
+	redeclaration := false
+	capture_scope := 0
+	for diagnostic in diagnostics.items {
+		count_mismatches += 1 if strings.contains(diagnostic.message, "unwrap has") else 0
+		duplicate = duplicate || strings.contains(diagnostic.message, "unwrap captures must have distinct names")
+		non_optional = non_optional || strings.contains(diagnostic.message, "unwrap requires an optional value")
+		guard = guard || strings.contains(diagnostic.message, "unwrap guard must be a bool")
+		outer_operand_scope = outer_operand_scope || strings.contains(diagnostic.message, "unresolved global 'earlier'")
+		immutable = immutable || strings.contains(diagnostic.message, "cannot assign immutable local 'value'")
+		redeclaration = redeclaration || strings.contains(diagnostic.message, "duplicate local 'value'")
+		capture_scope += 1 if strings.contains(diagnostic.message, "unresolved global 'value'") else 0
+	}
+	testing.expect_value(t, count_mismatches, 2)
+	testing.expect(t, duplicate)
+	testing.expect(t, non_optional)
+	testing.expect(t, guard)
+	testing.expect(t, outer_operand_scope)
+	testing.expect(t, immutable)
+	testing.expect(t, redeclaration)
+	testing.expect_value(t, capture_scope, 2)
+}
+
 @(test)
 if_unwrap_binding_is_scoped_to_then_block :: proc(t: ^testing.T) {
 	// The binding `v` is usable in the then-block but not in the else-block.

examples/programs/conditional_unwrap/main.bro

@@ -1,6 +1,9 @@
-# Milestone 5: conditional unwrapping `if opt |v| { ... }`.
+# Milestone 5: conditional optional unwrapping, guards, and multi-unwrap.
-# Tests a present optional binds and unwraps, a none takes the else branch, and
+
-# that optional pointers (?*T) unwrap the same way.
+observe :: func(counter @mut i32, value ?i32) ?i32 {
+	counter^ = counter^ + 1
+	return value
+}
 
 main :: func() i32 {
 	total i32 = 0
@@ -34,5 +37,55 @@ main :: func() i32 {
 		total = total + 1000
 	}
 
+	# guarded multi-unwrap exposes every capture to the guard and then-block
+	age ?i32 = 2
+	if a and age |value, years : value + years == 42| {
+		total = total
+	} else {
+		total = total + 100
+	}
+
+	# parenthesized chains and three-value unwraps are equivalent
+	bonus ?i32 = 0
+	if (a and age and bonus) |value, years, extra : value + years + extra == 42| {
+		total = total
+	} else {
+		total = total + 100
+	}
+
+	# false guards use the else branch, or simply fall through without one
+	if a |value : value == 0| {
+		total = total + 100
+	} else {
+		total = total
+	}
+	if a |value : value == 0| {
+		total = total + 100
+	}
+
+	# a failed unwrap prevents later expressions from being evaluated
+	calls i32 = 0
+	if b and observe(&calls, age) |missing, observed| {
+		total = total + missing + observed
+	}
+	if calls != 0 {
+		total = total + 100
+	}
+
+	# short-circuiting also applies after an earlier successful unwrap
+	if a and b and observe(&calls, age) |value, missing, observed| {
+		total = total + value + missing + observed
+	}
+	if calls != 0 {
+		total = total + 100
+	}
+
+	# optional pointers participate in multi-unwrap and guards
+	if a and p |value, q : value == 40 and q^ == 0| {
+		total = total
+	} else {
+		total = total + 100
+	}
+
 	return total                   # expect exit code 42
 }