diff --git a/pkg/analyze/text_analyze.go b/pkg/analyze/text_analyze.go
index 2477fe11..a320b74e 100644
--- a/pkg/analyze/text_analyze.go
+++ b/pkg/analyze/text_analyze.go
@@ -97,7 +97,27 @@ func analyzeRegexPattern(pattern string, collected []byte, outcomes []*troublesh
 		IconURI: "https://troubleshoot.sh/images/analyzer-icons/text-analyze.svg",
 	}
 
-	if re.MatchString(string(collected)) {
+	reMatch := re.MatchString(string(collected))
+	failWhen := false
+	if failOutcome.When != "" {
+		failWhen, err = strconv.ParseBool(failOutcome.When)
+		if err != nil {
+			return nil, errors.Wrapf(err, "failed to process when statement: %s", failOutcome.When)
+		}
+	}
+	passWhen := true
+	if passOutcome.When != "" {
+		passWhen, err = strconv.ParseBool(passOutcome.When)
+		if err != nil {
+			return nil, errors.Wrapf(err, "failed to process when statement: %s", passOutcome.When)
+		}
+	}
+
+	if passWhen == failWhen {
+		return nil, errors.Wrap(err, "outcome when conditions for fail and pass are equal")
+	}
+
+	if reMatch == passWhen {
 		result.IsPass = true
 		if passOutcome != nil {
 			result.Message = passOutcome.Message
@@ -105,6 +125,7 @@ func analyzeRegexPattern(pattern string, collected []byte, outcomes []*troublesh
 		}
 		return &result, nil
 	}
+
 	result.IsFail = true
 	if failOutcome != nil {
 		result.Message = failOutcome.Message
diff --git a/pkg/analyze/text_analyze_test.go b/pkg/analyze/text_analyze_test.go
index 55d47b6b..51f036f0 100644
--- a/pkg/analyze/text_analyze_test.go
+++ b/pkg/analyze/text_analyze_test.go
@@ -302,6 +302,42 @@ func Test_textAnalyze(t *testing.T) {
 				"text-collector-2/cfile-3.txt": []byte("Yes it all succeeded"),
 			},
 		},
+		{
+			name: "Fail on error case 1", // regexes are not case insensitive by default
+			analyzer: troubleshootv1beta2.TextAnalyze{
+				Outcomes: []*troubleshootv1beta2.Outcome{
+					{
+						Pass: &troubleshootv1beta2.SingleOutcome{
+							Message: "pass",
+							When:    "false",
+						},
+					},
+					{
+						Fail: &troubleshootv1beta2.SingleOutcome{
+							Message: "fail",
+							When:    "true",
+						},
+					},
+				},
+				CollectorName: "text-collector-1",
+				FileName:      "cfile-1.txt",
+				RegexPattern:  "error",
+			},
+			expectResult: []AnalyzeResult{
+				{
+					IsPass:  false,
+					IsWarn:  false,
+					IsFail:  true,
+					Title:   "text-collector-1",
+					Message: "fail",
+					IconKey: "kubernetes_text_analyze",
+					IconURI: "https://troubleshoot.sh/images/analyzer-icons/text-analyze.svg",
+				},
+			},
+			files: map[string][]byte{
+				"text-collector-1/cfile-1.txt": []byte("There is an error."),
+			},
+		},
 		{
 			name: "case insensitive failure case 1", // regexes are not case insensitive by default
 			analyzer: troubleshootv1beta2.TextAnalyze{