diff --git a/tools/go.mod b/tools/go.mod
index 1660b4cbf..7257b66fe 100644
--- a/tools/go.mod
+++ b/tools/go.mod
@@ -12,11 +12,9 @@ require (
 	github.com/creachadair/command v0.1.13
 	github.com/creachadair/flax v0.0.0-20240525192034-44db93b3a8ad
 	github.com/creachadair/mds v0.15.2
-	github.com/google/go-github/v63 v63.0.0
+	github.com/creachadair/taskgroup v0.9.0
+	github.com/google/go-github/v67 v67.0.0
 	github.com/natefinch/atomic v1.0.1
 )
 
-require (
-	github.com/creachadair/taskgroup v0.9.0 // indirect
-	github.com/google/go-querystring v1.1.0 // indirect
-)
+require github.com/google/go-querystring v1.1.0 // indirect
diff --git a/tools/go.sum b/tools/go.sum
index 09822230a..31fffa06b 100644
--- a/tools/go.sum
+++ b/tools/go.sum
@@ -6,11 +6,13 @@ github.com/creachadair/mds v0.15.2 h1:es1qGKgRGSaztpvrSQcZ0B9I6NsHYJ1Sa9naD/3OfC
 github.com/creachadair/mds v0.15.2/go.mod h1:4vrFYUzTXMJpMBU+OA292I6IUxKWCCfZkgXg+/kBZMo=
 github.com/creachadair/taskgroup v0.9.0 h1:kzXSea5C7R5DtnKFBOTEW3hvmCkiVnRkODMVDMgSS6k=
 github.com/creachadair/taskgroup v0.9.0/go.mod h1:+1hJc8zL1rQkxcMVqEYJ0UPGtwl6Iz1+fd4zcOLtt+A=
+github.com/fortytw2/leaktest v1.3.0 h1:u8491cBMTQ8ft8aeV+adlcytMZylmA5nnwwkRZjI8vw=
+github.com/fortytw2/leaktest v1.3.0/go.mod h1:jDsjWgpAGjm2CA7WthBh/CdZYEPF31XHquHwclZch5g=
 github.com/google/go-cmp v0.5.2/go.mod h1:v8dTdLbMG2kIc/vJvl+f65V22dbkXbowE6jgT/gNBxE=
 github.com/google/go-cmp v0.6.0 h1:ofyhxvXcZhMsU5ulbFiLKl/XBFqE1GSq7atu8tAmTRI=
 github.com/google/go-cmp v0.6.0/go.mod h1:17dUlkBOakJ0+DkrSSNjCkIjxS6bF9zb3elmeNGIjoY=
-github.com/google/go-github/v63 v63.0.0 h1:13xwK/wk9alSokujB9lJkuzdmQuVn2QCPeck76wR3nE=
-github.com/google/go-github/v63 v63.0.0/go.mod h1:IqbcrgUmIcEaioWrGYei/09o+ge5vhffGOcxrO0AfmA=
+github.com/google/go-github/v67 v67.0.0 h1:g11NDAmfaBaCO8qYdI9fsmbaRipHNWRIU/2YGvlh4rg=
+github.com/google/go-github/v67 v67.0.0/go.mod h1:zH3K7BxjFndr9QSeFibx4lTKkYS3K9nDanoI1NjaOtY=
 github.com/google/go-querystring v1.1.0 h1:AnCroh3fv4ZBgVIf1Iwtovgjaw/GiKJo8M8yD/fhyJ8=
 github.com/google/go-querystring v1.1.0/go.mod h1:Kcdr2DB4koayq7X8pmAG4sNG59So17icRSOU623lUBU=
 github.com/natefinch/atomic v1.0.1 h1:ZPYKxkqQOx3KZ+RsbnP/YsgvxWQPGxjC0oBt2AhwV0A=
diff --git a/tools/internal/github/pr.go b/tools/internal/github/pr.go
index 69e683d89..ad16706f5 100644
--- a/tools/internal/github/pr.go
+++ b/tools/internal/github/pr.go
@@ -9,7 +9,7 @@ import (
 	"os"
 	"time"
 
-	"github.com/google/go-github/v63/github"
+	"github.com/google/go-github/v67/github"
 )
 
 // Client is a GitHub API client that performs PSL-specific
@@ -185,3 +185,11 @@ func (c *Repo) PSLForHash(ctx context.Context, hash string) ([]byte, error) {
 	}
 	return []byte(ret), nil
 }
+
+func (c *Repo) LabelPullRequest(ctx context.Context, prNum int, labels []string) error {
+	ctx, cancel := context.WithTimeout(ctx, 5*time.Second)
+	defer cancel()
+
+	_, _, err := c.apiClient().Issues.ReplaceLabelsForIssue(ctx, c.owner(), c.repo(), prNum, labels)
+	return err
+}
diff --git a/tools/psltool/errors.go b/tools/psltool/errors.go
new file mode 100644
index 000000000..01d5693b9
--- /dev/null
+++ b/tools/psltool/errors.go
@@ -0,0 +1,100 @@
+package main
+
+import (
+	"errors"
+	"reflect"
+
+	"github.com/publicsuffix/list/tools/internal/parser"
+)
+
+const (
+	invalidTag  = "❌invalid"
+	dnsFailTag  = "❌FAIL - DNS VALIDATION"
+	sortFailTag = "❌FAIL - FIX SORTING ⏬"
+)
+
+var errToLabel = map[error]string{
+	// all parser errors, sort in alphabetical order
+	//parser.ErrCommentPreventsSectionSort{}:    "",
+	parser.ErrConflictingSuffixAndException{}: invalidTag,
+	//parser.ErrCommentPreventsSuffixSort{}:     "",
+	parser.ErrDuplicateSection{}:     invalidTag,
+	parser.ErrDuplicateSuffix{}:      invalidTag,
+	parser.ErrInvalidEncoding{}:      invalidTag,
+	parser.ErrInvalidSuffix{}:        invalidTag,
+	parser.ErrInvalidUnicode{}:       invalidTag,
+	parser.ErrMissingEntityEmail{}:   invalidTag,
+	parser.ErrMissingEntityName{}:    invalidTag,
+	parser.ErrMissingSection{}:       invalidTag,
+	parser.ErrMissingTXTRecord{}:     dnsFailTag,
+	parser.ErrMismatchedSection{}:    invalidTag,
+	parser.ErrNestedSection{}:        invalidTag,
+	parser.ErrSectionInSuffixBlock{}: invalidTag,
+	parser.ErrTXTCheckFailure{}:      dnsFailTag,
+	parser.ErrTXTRecordMismatch{}:    dnsFailTag,
+	parser.ErrUnclosedSection{}:      invalidTag,
+	parser.ErrUnknownSection{}:       invalidTag,
+	parser.ErrUnknownSectionMarker{}: invalidTag,
+	parser.ErrUnknownSectionMarker{}: invalidTag,
+	parser.ErrUnclosedSection{}:      invalidTag,
+
+	// all other errors
+	ErrReformat: sortFailTag,
+}
+
+var (
+	ErrReformat = errors.New("file needs reformatting, run 'psltool fmt' to fix")
+)
+
+func errorsToLabels(errs []error) []string {
+	labels := make([]string, 0, len(errs))
+
+	var (
+		sortSuccess = true
+		dnsSuccess  = true
+	)
+	setLabel := func(label string) {
+		switch label {
+		case sortFailTag:
+			sortSuccess = false
+		case dnsFailTag:
+			dnsSuccess = false
+		}
+		labels = append(labels, label)
+	}
+
+	for _, err := range errs {
+		if label, ok := errToLabel[err]; ok {
+			setLabel(label)
+			continue
+		}
+		for tpl, label := range errToLabel {
+			if isType(err, tpl) {
+				setLabel(label)
+				break
+			}
+		}
+	}
+
+	if sortSuccess {
+		labels = append(labels, "✔️Sorting Validated")
+	}
+	if dnsSuccess {
+		labels = append(labels, "✔️DNS _psl Validated")
+	}
+
+	return labels
+}
+
+func isType(err error, tpl error) bool {
+	if errors.Is(err, tpl) {
+		return true
+	}
+	if reflect.TypeOf(err) == reflect.TypeOf(tpl) {
+		return true
+	}
+	if wraped, ok := err.(interface{ Unwrap() error }); ok {
+		return isType(wraped.Unwrap(), tpl)
+	}
+	return false
+}
diff --git a/tools/psltool/psltool.go b/tools/psltool/psltool.go
index 5bcecbd55..b859e3c0b 100644
--- a/tools/psltool/psltool.go
+++ b/tools/psltool/psltool.go
@@ -258,7 +258,15 @@ func runCheckPR(env *command.Env, prStr string) error {
 
 	clean := after.MarshalPSL()
 	if !bytes.Equal(withPR, clean) {
-		errs = append(errs, errors.New("file needs reformatting, run 'psltool fmt' to fix"))
+		errs = append(errs, ErrReformat)
+	}
+
+	// Label the PR base on our errors
+	if len(errs) > 0 {
+		labels := errorsToLabels(errs)
+		if err := client.LabelPullRequest(env.Context(), pr, labels); err != nil {
+			return fmt.Errorf("failed to set labels on PR: %w", err)
+		}
 	}
 
 	// Print the blocks marked changed, so a human can check that