diff --git a/grype/matcher/common/distro_matchers.go b/grype/matcher/common/distro_matchers.go
index cb76097579d..94ae8693935 100644
--- a/grype/matcher/common/distro_matchers.go
+++ b/grype/matcher/common/distro_matchers.go
@@ -1,8 +1,11 @@
 package common
 
 import (
+	"errors"
 	"fmt"
 
+	"github.com/anchore/grype/internal/log"
+
 	"github.com/anchore/grype/grype/match"
 	"github.com/anchore/grype/grype/pkg"
 	"github.com/anchore/grype/grype/version"
@@ -32,7 +35,12 @@ func FindMatchesByPackageDistro(store vulnerability.ProviderByDistro, d *distro.
 		// if the constraint it met, then the given package has the vulnerability
 		isPackageVulnerable, err := vuln.Constraint.Satisfied(verObj)
 		if err != nil {
-			return nil, fmt.Errorf("distro matcher failed to check constraint='%s' version='%s': %w", vuln.Constraint, verObj, err)
+			var e *version.NonFatalConstraintError
+			if errors.As(err, &e) {
+				log.Warn(e)
+			} else {
+				return nil, fmt.Errorf("distro matcher failed to check constraint='%s' version='%s': %w", vuln.Constraint, verObj, err)
+			}
 		}
 
 		if !isPackageVulnerable {
diff --git a/grype/version/constraint.go b/grype/version/constraint.go
index b3d54a966e4..7a64d0d4c4f 100644
--- a/grype/version/constraint.go
+++ b/grype/version/constraint.go
@@ -40,3 +40,17 @@ func MustGetConstraint(constStr string, format Format) Constraint {
 	}
 	return constraint
 }
+
+// NonFatalConstraintError should be used any time an unexpected but recoverable condition is encountered while
+// checking version constraint satisfaction. The error should get returned by any implementer of the Constraint
+// interface. If returned by the Satisfied method on the Constraint interface, this error will be caught and
+// logged as a warning in the FindMatchesByPackageDistro function in grype/matcher/common/distro_matchers.go
+type NonFatalConstraintError struct {
+	constraint Constraint
+	version    *Version
+	message    string
+}
+
+func (e NonFatalConstraintError) Error() string {
+	return fmt.Sprintf("Matching raw constraint %s against version %s caused a non-fatal error: %s", e.constraint, e.version, e.message)
+}
diff --git a/grype/version/kb_contraint.go b/grype/version/kb_contraint.go
index 7bb227a7066..dc8d2e92365 100644
--- a/grype/version/kb_contraint.go
+++ b/grype/version/kb_contraint.go
@@ -37,14 +37,16 @@ func (c kbConstraint) supported(format Format) bool {
 }
 
 func (c kbConstraint) Satisfied(version *Version) (bool, error) {
-	if c.raw == "" && version != nil {
-		// an empty constraint is always satisfied
-		return true, nil
-	} else if version == nil {
-		if c.raw != "" {
-			// a non-empty constraint with no version given should always fail
-			return false, nil
+	if c.raw == "" {
+		// an empty constraint is never satisfied
+		return false, &NonFatalConstraintError{
+			constraint: c,
+			version:    version,
+			message:    "Unexpected data in DB: Empty raw version constraint.",
 		}
+	}
+
+	if version == nil {
 		return true, nil
 	}
 
@@ -57,7 +59,7 @@ func (c kbConstraint) Satisfied(version *Version) (bool, error) {
 
 func (c kbConstraint) String() string {
 	if c.raw == "" {
-		return "none (kb)"
+		return fmt.Sprintf("%q (kb)", c.raw)
 	}
 	return fmt.Sprintf("%s (kb)", c.raw)
 }
diff --git a/grype/version/kb_contraint_test.go b/grype/version/kb_contraint_test.go
index 6d2ba8ab455..d6b5348e89f 100644
--- a/grype/version/kb_contraint_test.go
+++ b/grype/version/kb_contraint_test.go
@@ -1,28 +1,54 @@
 package version
 
 import (
-	"errors"
+	"github.com/stretchr/testify/assert"
 	"testing"
 )
 
 func TestVersionKbConstraint(t *testing.T) {
-	tests := []testCase{
-		{version: "", constraint: "", satisfied: true},
-		{version: "", constraint: "foo", satisfied: false},
-		{version: "1", constraint: "foo", satisfied: false},
-		{version: "1", constraint: "1", satisfied: true},
-		{version: "878787", constraint: "979797 || 101010 || 878787", satisfied: true},
-		{version: "478787", constraint: "979797 || 101010 || 878787", satisfied: false},
+	tests := []struct {
+		name           string
+		version        string
+		constraint     string
+		satisfied      bool
+		shouldErr      bool
+		errorAssertion func(t *testing.T, err error)
+	}{
+		{name: "no constraint no version raises error", version: "", constraint: "", satisfied: false, shouldErr: true, errorAssertion: func(t *testing.T, err error) {
+			var expectedError *NonFatalConstraintError
+			assert.ErrorAs(t, err, &expectedError, "Unexpected error type from kbConstraint.Satisfied: %v", err)
+		}},
+		{name: "no constraint with version raises error", version: "878787", constraint: "", satisfied: false, shouldErr: true, errorAssertion: func(t *testing.T, err error) {
+			var expectedError *NonFatalConstraintError
+			assert.ErrorAs(t, err, &expectedError, "Unexpected error type from kbConstraint.Satisfied: %v", err)
+		}},
+		{name: "no version is unsatisifed", version: "", constraint: "foo", satisfied: false},
+		{name: "version constraint mismatch", version: "1", constraint: "foo", satisfied: false},
+		{name: "matching version and constraint", version: "1", constraint: "1", satisfied: true},
+		{name: "base keyword matching version and constraint", version: "base", constraint: "base", satisfied: true},
+		{name: "version and OR constraint match", version: "878787", constraint: "979797 || 101010 || 878787", satisfied: true},
+		{name: "version and OR constraint mismatch", version: "478787", constraint: "979797 || 101010 || 878787", satisfied: false},
 	}
 
 	for _, test := range tests {
-		t.Run(test.name(), func(t *testing.T) {
+		t.Run(test.name, func(t *testing.T) {
 			constraint, err := newKBConstraint(test.constraint)
-			if !errors.Is(err, test.constErr) {
-				t.Fatalf("unexpected constraint error: '%+v'!='%+v'", err, test.constErr)
-			}
+			assert.NoError(t, err, "unexpected error from newKBConstraint: %v", err)
+
+			version, err := NewVersion(test.version, KBFormat)
+			assert.NoError(t, err, "unexpected error from NewVersion: %v", err)
 
-			test.assert(t, KBFormat, constraint)
+			isSatisfied, err := constraint.Satisfied(version)
+			if test.shouldErr {
+				if test.errorAssertion != nil {
+					test.errorAssertion(t, err)
+				} else {
+					assert.Error(t, err)
+				}
+			} else {
+				assert.NoError(t, err, "unexpected error from kbConstraint.Satisfied: %v", err)
+			}
+			assert.Equal(t, test.satisfied, isSatisfied, "unexpected constraint check result")
 		})
 	}
 }