diff --git a/docs/roadmap/remediation.md b/docs/roadmap/remediation.md
index fec84c3..5837883 100644
--- a/docs/roadmap/remediation.md
+++ b/docs/roadmap/remediation.md
@@ -251,7 +251,7 @@ value was prohibited. The complete offline root suite passed on Go 1.26.8.
 
 ## R-7: Retain entered flag spellings in parser-level usage failures
 
-Status: open. Priority: P3. Category: incomplete diagnostic adaptation.
+Status: complete. Priority: P3. Category: incomplete diagnostic adaptation.
 
 **Evidence:** Typed flag conversion uses occurrence provenance, but
 [Session.Parse](../../internal/cobra/parse.go#L89) returns normalized backend
@@ -278,6 +278,15 @@ values and invalid help values, including an earlier invalid occurrence followed
 by a valid overwrite. Assert the identifying fragments and existing causes
 where supported; no new exact diagnostic format is required.
 
+**Completed:** Missing-value failures now carry the entered long/short spelling
+through a neutral adapter record; earlier backend failures retain precedence.
+Built-in help conversion uses the failing occurrence's original spelling,
+including when a later valid value follows it. Adapter and public-boundary
+regressions failed before the fix and now cover alias values, clusters, help
+occurrences, entered usage paths, and input-initialization avoidance. Existing
+usage classification is unchanged. The complete offline root suite passed on
+Go 1.26.8.
+
 ## R-8: Reconcile the completed feature roadmap's historical descriptions
 
 Status: open. Priority: P3. Category: documentation drift.
diff --git a/internal/cobra/flags.go b/internal/cobra/flags.go
index d6c6505..e87fabe 100644
--- a/internal/cobra/flags.go
+++ b/internal/cobra/flags.go
@@ -1,12 +1,13 @@
 package cobra
 
 import (
+	"fmt"
 	"strings"
 
 	commandmeta "gitea.maximumdirect.net/eric/CommandKit/internal/commandmeta"
 )
 
-func interpretFlagTokens(argv []string, flags []commandmeta.Flag, aliases []commandmeta.FlagAlias) ([]string, map[string][]string) {
+func interpretFlagTokens(argv []string, flags []commandmeta.Flag, aliases []commandmeta.FlagAlias) ([]string, map[string][]string, *commandmeta.Failure) {
 	canonical := make(map[string]commandmeta.Flag, len(flags)*2+2)
 	help := commandmeta.Flag{Name: "help", Short: "h", Boolean: true}
 	canonical["--help"] = help
@@ -61,6 +62,9 @@ func interpretFlagTokens(argv []string, flags []commandmeta.Flag, aliases []comm
 				index += 2
 				continue
 			}
+			if !flag.Boolean {
+				return interpreted, spellings, &commandmeta.Failure{Message: fmt.Sprintf("flag needs an argument: %s", original)}
+			}
 			interpreted = append(interpreted, "--"+flag.Name)
 			index++
 			continue
@@ -107,8 +111,7 @@ func interpretFlagTokens(argv []string, flags []commandmeta.Flag, aliases []comm
 					consumedNext = true
 					break
 				}
-				interpreted = append(interpreted, "--"+flag.Name)
-				break
+				return interpreted, spellings, &commandmeta.Failure{Message: fmt.Sprintf("flag needs an argument: %s", original)}
 			}
 			if !consumedNext {
 				index++
@@ -118,5 +121,5 @@ func interpretFlagTokens(argv []string, flags []commandmeta.Flag, aliases []comm
 		interpreted = append(interpreted, token)
 		index++
 	}
-	return interpreted, spellings
+	return interpreted, spellings, nil
 }
diff --git a/internal/cobra/flags_test.go b/internal/cobra/flags_test.go
index fc0fd0f..8a5695e 100644
--- a/internal/cobra/flags_test.go
+++ b/internal/cobra/flags_test.go
@@ -2,6 +2,7 @@ package cobra
 
 import (
 	"reflect"
+	"strings"
 	"testing"
 
 	commandmeta "gitea.maximumdirect.net/eric/CommandKit/internal/commandmeta"
@@ -158,3 +159,40 @@ func TestParseFlagAliasOccurrenceOrderAndSpellings(t *testing.T) {
 		t.Fatalf("tag spellings = %#v, want %#v", got, want)
 	}
 }
+
+func TestParseFailuresRetainEnteredFlagSpellings(t *testing.T) {
+	for _, spelling := range []string{"--color", "--colour", "-c", "-C"} {
+		t.Run("missing/"+spelling, func(t *testing.T) {
+			result := Parse(flagGrammarTree(), []string{"run", spelling}, flagGrammarOptions())
+			if result.Failure == nil || !strings.Contains(result.Failure.Message, ": "+spelling) {
+				t.Fatalf("missing value failure = %#v, want entered spelling %q", result.Failure, spelling)
+			}
+		})
+	}
+	result := Parse(flagGrammarTree(), []string{"run", "-wC"}, flagGrammarOptions())
+	if result.Failure == nil || !strings.Contains(result.Failure.Message, ": -C") {
+		t.Fatalf("cluster missing value failure = %#v", result.Failure)
+	}
+	for _, test := range []struct {
+		args     []string
+		spelling string
+	}{
+		{[]string{"--hlep=bad"}, "--hlep"},
+		{[]string{"-h=bad"}, "-h"},
+		{[]string{"--help=bad"}, "--help"},
+		{[]string{"--hlep=bad", "--help=true"}, "--hlep"},
+		{[]string{"-h=bad", "--hlep=true"}, "-h"},
+		{[]string{"--help=true", "--hlep=bad"}, "--hlep"},
+	} {
+		t.Run(strings.Join(test.args, " "), func(t *testing.T) {
+			result := Parse(flagGrammarTree(), append([]string{"run"}, test.args...), flagGrammarOptions())
+			if result.Failure == nil || !strings.Contains(result.Failure.Message, "for "+test.spelling) {
+				t.Fatalf("help failure = %#v, want entered spelling %q", result.Failure, test.spelling)
+			}
+		})
+	}
+	result = Parse(flagGrammarTree(), []string{"run", "--unknown", "--colour"}, flagGrammarOptions())
+	if result.Failure == nil || !strings.Contains(result.Failure.Message, "unknown") || strings.Contains(result.Failure.Message, "needs an argument") {
+		t.Fatalf("earlier parser failure = %#v", result.Failure)
+	}
+}
diff --git a/internal/cobra/parse.go b/internal/cobra/parse.go
index 9d469be..82e55a8 100644
--- a/internal/cobra/parse.go
+++ b/internal/cobra/parse.go
@@ -77,7 +77,7 @@ func (session *Session) Parse(argv []string) commandmeta.Result {
 	}
 
 	remaining := append(commandpath.CloneTokens(unconsumed), tail...)
-	interpreted, spellings := interpretFlagTokens(remaining, selectedNode.Flags, session.flagAliases)
+	interpreted, spellings, interpretationFailure := interpretFlagTokens(remaining, selectedNode.Flags, session.flagAliases)
 	for _, flag := range selectedNode.Flags {
 		if value := selected.Flags().Lookup(flag.Name); value != nil {
 			value.Value.(*rawValue).queueSpellings(spellings[flag.Name])
@@ -89,6 +89,12 @@ func (session *Session) Parse(argv []string) commandmeta.Result {
 	if err := selected.ParseFlags(interpreted); err != nil {
 		return failure(result, err.Error())
 	}
+	// Parse the completed prefix first so an earlier backend failure keeps its
+	// precedence over a missing value discovered while interpreting aliases.
+	if interpretationFailure != nil {
+		result.Failure = interpretationFailure
+		return result
+	}
 	operands := selected.Flags().Args()
 
 	result.Operands = append([]string(nil), operands...)
@@ -473,10 +479,14 @@ func (v *rawValue) spellingsCopy() []string { return append([]string(nil), v.spe
 
 func (v *rawValue) lastBool() (bool, error) {
 	var value bool
-	for _, raw := range v.values {
+	for index, raw := range v.values {
 		parsed, err := strconv.ParseBool(raw)
 		if err != nil {
-			return false, fmt.Errorf("invalid boolean value %q for --help", raw)
+			spelling := "--help"
+			if index < len(v.spellings) {
+				spelling = v.spellings[index]
+			}
+			return false, fmt.Errorf("invalid boolean value %q for %s", raw, spelling)
 		}
 		value = parsed
 	}
diff --git a/route_test.go b/route_test.go
index f6e3378..3eddc26 100644
--- a/route_test.go
+++ b/route_test.go
@@ -11,6 +11,46 @@ import (
 	"testing"
 )
 
+func TestParserFailuresRetainAliasUsageAndFlagSpellings(t *testing.T) {
+	built := 0
+	command := NewCommand(CommandSpec[struct{}]{
+		Name:     "inspect",
+		NewInput: func() struct{} { built++; return struct{}{} },
+		Flags: []Flag[struct{}]{ValueFlag(FlagMeta{Name: "format"}, (*string)(nil),
+			func(value string) (string, error) { return value, nil },
+			func(*struct{}, Supplied[string]) {})},
+		Run: func(Invocation, struct{}) Outcome { t.Fatal("invalid input executed"); return Success() },
+	})
+	app, err := New(Identity{Name: "Demo"}, command, Alias("i", "inspect"),
+		FlagAliasFor("inspect", "--fmt", "--format"),
+		FlagAliasFor("inspect", "-F", "--format"), FlagAlias("--hlep", "--help"))
+	if err != nil {
+		t.Fatal(err)
+	}
+	for _, test := range []struct {
+		args     []string
+		spelling string
+	}{
+		{[]string{"i", "--fmt"}, ": --fmt"},
+		{[]string{"i", "-F"}, ": -F"},
+		{[]string{"i", "--hlep=bad", "--help=true"}, "for --hlep"},
+		{[]string{"i", "-h=bad"}, "for -h"},
+	} {
+		t.Run(strings.Join(test.args, " "), func(t *testing.T) {
+			var diagnostics bytes.Buffer
+			outcome := app.Execute(context.Background(), test.args, Streams{Out: io.Discard, Err: &diagnostics})
+			if outcome.Kind != OutcomeUsage || built != 0 {
+				t.Fatalf("outcome = %#v, inputs built = %d", outcome, built)
+			}
+			for _, fragment := range []string{test.spelling, "Usage: Demo i", "Alias for: Demo inspect"} {
+				if !strings.Contains(diagnostics.String(), fragment) {
+					t.Errorf("diagnostics %q omit %q", diagnostics.String(), fragment)
+				}
+			}
+		})
+	}
+}
+
 func TestCommandContextSurvivesIncompleteAndInvalidOperandCounts(t *testing.T) {
 	for _, spelling := range []string{"run", "r"} {
 		for _, test := range []struct {