diff --git a/command/operator_diagnose.go b/command/operator_diagnose.go
index 4ffc03fed1..16884263f4 100644
--- a/command/operator_diagnose.go
+++ b/command/operator_diagnose.go
@@ -167,7 +167,7 @@ func (c *OperatorDiagnoseCommand) RunWithParsedFlags() int {
 		}
 	}
 	ctx := diagnose.Context(context.Background(), c.diagnose)
-	c.diagnose.SetSkipList(c.flagSkips)
+	c.diagnose.SkipFilters = c.flagSkips
 	err := c.offlineDiagnostics(ctx)
 
 	results := c.diagnose.Finalize(ctx)
diff --git a/vault/diagnose/helpers.go b/vault/diagnose/helpers.go
index 983dccacc9..3314a3635b 100644
--- a/vault/diagnose/helpers.go
+++ b/vault/diagnose/helpers.go
@@ -7,6 +7,7 @@ import (
 	"strings"
 	"time"
 
+	"github.com/hashicorp/vault/sdk/helper/strutil"
 	"go.opentelemetry.io/otel/attribute"
 	"go.opentelemetry.io/otel/codes"
 	sdktrace "go.opentelemetry.io/otel/sdk/trace"
@@ -38,10 +39,10 @@ var noopTracer = trace.NewNoopTracerProvider().Tracer("vault-diagnose")
 type testFunction func(context.Context) error
 
 type Session struct {
-	tc     *TelemetryCollector
-	tracer trace.Tracer
-	tp     *sdktrace.TracerProvider
-	skip   map[string]bool
+	tc          *TelemetryCollector
+	tracer      trace.Tracer
+	tp          *sdktrace.TracerProvider
+	SkipFilters []string
 }
 
 // New initializes a Diagnose tracing session.  In particular this wires a TelemetryCollector, which
@@ -60,21 +61,14 @@ func New(w io.Writer) *Session {
 		tp:     tp,
 		tc:     tc,
 		tracer: tracer,
-		skip:   make(map[string]bool),
 	}
 	return sess
 }
 
-func (s *Session) SetSkipList(ls []string) {
-	for _, e := range ls {
-		s.skip[e] = true
-	}
-}
-
-// IsSkipped returns true if skipName is present in the skip list.  Can be used in combination with Skip to mark a
-// span skipped and conditionally skip some logic.
-func (s *Session) IsSkipped(skipName string) bool {
-	return s.skip[skipName]
+// IsSkipped returns true if skipName is present in the SkipFilters list.  Can be used in combination with Skip to mark a
+// span skipped and conditionally skips some logic.
+func (s *Session) IsSkipped(spanName string) bool {
+	return strutil.StrListContainsCaseInsensitive(s.SkipFilters, spanName)
 }
 
 // Context returns a new context with a defined diagnose session
@@ -191,6 +185,12 @@ func addSpotCheckResult(ctx context.Context, eventName, checkName, message strin
 }
 
 func SpotCheck(ctx context.Context, checkName string, f func() error) error {
+	sess := CurrentSession(ctx)
+	if sess.IsSkipped(checkName) {
+		SpotSkipped(ctx, checkName, "skipped as requested")
+		return nil
+	}
+
 	err := f()
 	if err != nil {
 		SpotError(ctx, checkName, err)
@@ -206,6 +206,11 @@ func SpotCheck(ctx context.Context, checkName string, f func() error) error {
 func Test(ctx context.Context, spanName string, function testFunction, options ...trace.SpanOption) error {
 	ctx, span := StartSpan(ctx, spanName, options...)
 	defer span.End()
+	sess := CurrentSession(ctx)
+	if sess.IsSkipped(spanName) {
+		Skipped(ctx, "skipped as requested")
+		return nil
+	}
 
 	err := function(ctx)
 	if err != nil {
@@ -233,22 +238,6 @@ func WithTimeout(d time.Duration, f testFunction) testFunction {
 	}
 }
 
-// Skippable wraps a Test function with logic that will not run the test if the skipName
-// was in the session's skip list
-func Skippable(skipName string, f testFunction) testFunction {
-	return func(ctx context.Context) error {
-		session := CurrentSession(ctx)
-		if session != nil {
-			if !session.IsSkipped(skipName) {
-				return f(ctx)
-			} else {
-				Skipped(ctx, "skipped as requested")
-			}
-		}
-		return nil
-	}
-}
-
 // CapitalizeFirstLetter returns a string with the first letter capitalized
 func CapitalizeFirstLetter(msg string) string {
 	words := strings.Split(msg, " ")
diff --git a/vault/diagnose/helpers_test.go b/vault/diagnose/helpers_test.go
index 93995d2924..ecff4b49df 100644
--- a/vault/diagnose/helpers_test.go
+++ b/vault/diagnose/helpers_test.go
@@ -63,7 +63,7 @@ func TestDiagnoseOtelResults(t *testing.T) {
 		},
 	}
 	sess := New(os.Stdout)
-	sess.SetSkipList([]string{"dispose-grounds"})
+	sess.SkipFilters = []string{"dispose-grounds"}
 	ctx := Context(context.Background(), sess)
 
 	func() {
@@ -107,7 +107,7 @@ func makeCoffee(ctx context.Context) error {
 
 	SpotCheck(ctx, "pick-scone", pickScone)
 
-	Test(ctx, "dispose-grounds", Skippable("dispose-grounds", disposeGrounds))
+	Test(ctx, "dispose-grounds", disposeGrounds)
 	return nil
 }
 
diff --git a/vault/diagnose/output.go b/vault/diagnose/output.go
index 94035cd164..3eca7a0669 100644
--- a/vault/diagnose/output.go
+++ b/vault/diagnose/output.go
@@ -23,7 +23,7 @@ const (
 	status_ok      = "\u001b[32m[ success ]\u001b[0m "
 	status_failed  = "\u001b[31m[ failure ]\u001b[0m "
 	status_warn    = "\u001b[33m[ warning ]\u001b[0m "
-	status_skipped = "\u001b[90m[ skip ]\u001b[0m "
+	status_skipped = "\u001b[90m[ skipped ]\u001b[0m "
 	same_line      = "\x0d"
 	ErrorStatus    = 2
 	WarningStatus  = 1