diff --git a/test/e2e/annotations_test.go b/test/e2e/annotations_test.go
index 6952a371c..077340f5c 100644
--- a/test/e2e/annotations_test.go
+++ b/test/e2e/annotations_test.go
@@ -467,8 +467,9 @@ data:
 		require.NoErrorf(t, err, "Expected to successfully unmarshal")
 
 		_, versionedAnnExists := respKubectl.Annotations["kapp.k14s.io/versioned"]
-		isConditionsMet := respKubectl.Kind == "ConfigMap" || respKubectl.Name == "config" || versionedAnnExists
-		require.True(t, isConditionsMet, "Expected to have versioned ConfigMap resource")
+		require.Condition(t, func() bool {
+			return respKubectl.Kind == "ConfigMap" && respKubectl.Name == "config" && versionedAnnExists
+		}, "Expected to have versioned ConfigMap resource")
 
 		kappOut, _ := kapp.RunWithOpts([]string{"deploy", "-f", "-", "-a", name, "--json"},
 			RunOpts{IntoNs: true, StdinReader: strings.NewReader(yaml)})
diff --git a/test/e2e/cluster_resource.go b/test/e2e/cluster_resource.go
index aaad82773..2e4ffacb0 100644
--- a/test/e2e/cluster_resource.go
+++ b/test/e2e/cluster_resource.go
@@ -42,9 +42,9 @@ func NewPresentClusterResource(kind, name, ns string, kubectl Kubectl) ClusterRe
 
 func NewMissingClusterResource(t *testing.T, kind, name, ns string, kubectl Kubectl) {
 	_, err := kubectl.RunWithOpts([]string{"get", kind, name, "-n", ns, "-o", "yaml"}, RunOpts{AllowError: true})
-	isConditionsMet := err != nil || strings.Contains(err.Error(), "Error from server (NotFound)")
-
-	require.True(t, isConditionsMet, "Expected resource to not exist")
+	require.Condition(t, func() bool {
+		return err != nil && strings.Contains(err.Error(), "Error from server (NotFound)")
+	}, "Expected resource to not exist")
 }
 
 func (r ClusterResource) UID() string {
diff --git a/test/e2e/common.go b/test/e2e/common.go
index 980f17848..c0702d546 100644
--- a/test/e2e/common.go
+++ b/test/e2e/common.go
@@ -19,8 +19,8 @@ func validateChanges(t *testing.T, respTable []ui.JSONUITableResp, expected []ma
 		delete(row, "age")
 	}
 
-	require.Exactlyf(t, expected, respTable[0].Rows, "Expected to see correct changes, but did not")
-	require.Equalf(t, notesOp, respTable[0].Notes[0], "Expected to see correct summary, but did not")
-	require.Equalf(t, notesWaitTo, respTable[0].Notes[1], "Expected to see correct summary, but did not")
+	require.Exactlyf(t, expected, respTable[0].Rows, "Expected to see correct changes, but did not: '%s'", output)
+	require.Equalf(t, notesOp, respTable[0].Notes[0], "Expected to see correct summary, but did not: '%s'", output)
+	require.Equalf(t, notesWaitTo, respTable[0].Notes[1], "Expected to see correct summary, but did not: '%s'", output)
 
 }
diff --git a/test/e2e/config_test.go b/test/e2e/config_test.go
index fe82b7916..30b52b64c 100644
--- a/test/e2e/config_test.go
+++ b/test/e2e/config_test.go
@@ -193,7 +193,7 @@ secrets:
 		secrets := NewPresentClusterResource("serviceaccount", "test-sa-with-secrets", env.Namespace, kubectl).RawPath(ctlres.NewPathFromStrings([]string{"secrets"})).([]interface{})
 
 		require.Len(t, secrets, 2, "Expected one set and one generated secret")
-		require.Exactlyf(t, map[string]interface{}{"name": "some-secret"}, secrets[0], "Expected provided secret")
+		require.Exactlyf(t, map[string]interface{}{"name": "some-secret"}, secrets[0], "Expected provided secret at idx0: %#v", secrets[0])
 
 		generatedSecretName = secrets[1].(map[string]interface{})["name"].(string)
 		require.True(t, strings.HasPrefix(generatedSecretName, "test-sa-with-secrets-token-"), "Expected generated secret at idx1: %#v", secrets[1])
@@ -247,9 +247,9 @@ secrets:
 
 		secrets = NewPresentClusterResource("serviceaccount", "test-sa-without-secrets", env.Namespace, kubectl).RawPath(ctlres.NewPathFromStrings([]string{"secrets"})).([]interface{})
 
-		require.True(t, strings.HasPrefix(secrets[1].(map[string]interface{})["name"].(string), "test-sa-without-secrets-token-"), "Expected generated secret at idx1: %#v", secrets[1])
 		require.Len(t, secrets, 2, "Expected one set and one generated secret")
 		require.Exactlyf(t, map[string]interface{}{"name": "some-secret"}, secrets[0], "Expected provided secret at idx0")
+		require.True(t, strings.HasPrefix(secrets[1].(map[string]interface{})["name"].(string), "test-sa-without-secrets-token-"), "Expected generated secret at idx1: %#v", secrets[1])
 
 	})
 
diff --git a/test/e2e/diff_test.go b/test/e2e/diff_test.go
index d542ee399..ea6b499f3 100644
--- a/test/e2e/diff_test.go
+++ b/test/e2e/diff_test.go
@@ -240,6 +240,7 @@ func TestDiffExitStatus(t *testing.T) {
 		RunOpts{IntoNs: true, AllowError: true, StdinReader: strings.NewReader("---\n")})
 
 	require.Errorf(t, err, "Expected to receive error")
+
 	require.Containsf(t, err.Error(), "Exiting after diffing with no pending changes (exit status 2)", "Expected to find stderr output")
 	require.Containsf(t, err.Error(), "exit code: '2'", "Expected to find exit code")
 
@@ -255,6 +256,7 @@ metadata:
 		RunOpts{IntoNs: true, AllowError: true, StdinReader: strings.NewReader(yaml1)})
 
 	require.Errorf(t, err, "Expected to receive error")
+
 	require.Containsf(t, err.Error(), "Exiting after diffing with pending changes (exit status 3)", "Expected to find stderr output")
 	require.Containsf(t, err.Error(), "exit code: '3'", "Expected to find exit code")
 }
diff --git a/test/e2e/env.go b/test/e2e/env.go
index 3514576ae..20c84cddb 100644
--- a/test/e2e/env.go
+++ b/test/e2e/env.go
@@ -4,10 +4,11 @@
 package e2e
 
 import (
-	"github.com/stretchr/testify/require"
 	"os"
 	"strings"
 	"testing"
+
+	"github.com/stretchr/testify/require"
 )
 
 type Env struct {
diff --git a/test/e2e/filter_test.go b/test/e2e/filter_test.go
index c165d44ba..1e9219aaf 100644
--- a/test/e2e/filter_test.go
+++ b/test/e2e/filter_test.go
@@ -4,9 +4,10 @@
 package e2e
 
 import (
-	"github.com/stretchr/testify/require"
 	"strings"
 	"testing"
+
+	"github.com/stretchr/testify/require"
 )
 
 func TestFilter(t *testing.T) {
diff --git a/test/e2e/formatted_error_test.go b/test/e2e/formatted_error_test.go
index 593d2a676..d19d24c7c 100644
--- a/test/e2e/formatted_error_test.go
+++ b/test/e2e/formatted_error_test.go
@@ -4,10 +4,11 @@
 package e2e
 
 import (
-	"github.com/stretchr/testify/require"
 	"regexp"
 	"strings"
 	"testing"
+
+	"github.com/stretchr/testify/require"
 )
 
 func TestFormattedError(t *testing.T) {
@@ -71,11 +72,6 @@ kapp: Error: Applying create job/successful-job (batch/v1) namespace: default:
 		replaceUIDs := regexp.MustCompile(`"controller-uid":"[^"]+"`)
 		out = replaceUIDs.ReplaceAllString(out, "-replaced-")
 
-		require.Containsf(t, out, expectedErr, "Expected to see expected err in output, but did not: %d chars >>>%s<<< vs %d chars >>>%s<<<",
-			len(out), replaceSpace(out), len(expectedErr), replaceSpace(expectedErr))
+		require.Containsf(t, out, expectedErr, "Expected to see expected err in output, but did not")
 	})
 }
-
-func replaceSpace(in string) string {
-	return strings.ReplaceAll(in, " ", "#")
-}
diff --git a/test/e2e/help_test.go b/test/e2e/help_test.go
index f6d0a64f9..ccaf5382e 100644
--- a/test/e2e/help_test.go
+++ b/test/e2e/help_test.go
@@ -13,8 +13,7 @@ func TestHelpCommandGroup(t *testing.T) {
 	kapp := Kapp{t, env.Namespace, env.KappBinaryPath, Logger{}}
 
 	_, err := kapp.RunWithOpts([]string{"app-group"}, RunOpts{NoNamespace: true, AllowError: true})
-
 	require.Errorf(t, err, "Expected to receive error")
-	require.Contains(t, err.Error(), "Error: Use one of available subcommands: delete, deploy",
-		"Expected helpful error message")
+
+	require.Contains(t, err.Error(), "Error: Use one of available subcommands: delete, deploy", "Expected helpful error message")
 }
diff --git a/test/e2e/ignore_failing_api_services_flag_test.go b/test/e2e/ignore_failing_api_services_flag_test.go
index 2beec80cf..2fbbcd5ef 100644
--- a/test/e2e/ignore_failing_api_services_flag_test.go
+++ b/test/e2e/ignore_failing_api_services_flag_test.go
@@ -128,8 +128,8 @@ metadata:
 	logger.Section("deploy app that uses failing api service", func() {
 		_, err := kapp.RunWithOpts([]string{"deploy", "-f", "-", "-a", name3}, RunOpts{
 			AllowError: true, IntoNs: true, StdinReader: strings.NewReader(yaml3)})
-
 		require.Errorf(t, err, "Expected error when deploying with failing api service")
+
 		require.Contains(t, err.Error(), "unable to retrieve the complete list of server APIs: dummykapptest.com/v1: the server is currently unable to handle the request",
 			"Expected api retrieval error")
 	})
@@ -139,10 +139,9 @@ metadata:
 
 		_, err := kapp.RunWithOpts([]string{"deploy", "-f", "-", "-a", name3, ignoreFlag}, RunOpts{
 			AllowError: true, IntoNs: true, StdinReader: strings.NewReader(yaml3)})
-
 		require.Errorf(t, err, "Expected error when deploying with failing api service")
-		require.Contains(t, err.Error(), "Expected to find kind 'dummykapptest.com/v1/Foo', but did not",
-			"Expected CRD retrieval error")
+
+		require.Contains(t, err.Error(), "Expected to find kind 'dummykapptest.com/v1/Foo', but did not", "Expected CRD retrieval error")
 	})
 
 	logger.Section("delete app that does not use api service", func() {
@@ -279,10 +278,9 @@ spec: {}
 	logger.Section("deploy app that uses failing group version", func() {
 		_, err := kapp.RunWithOpts([]string{"deploy", "-f", "-", "-a", name3, "--apply-timeout=5s"}, RunOpts{
 			AllowError: true, IntoNs: true, StdinReader: strings.NewReader(yaml3)})
-
 		require.Errorf(t, err, "Expected error when deploying with failing group version")
-		require.Contains(t, err.Error(), `service "failing-group-version-webhook" not found`,
-			"Expected api retrieval error")
+
+		require.Contains(t, err.Error(), `service "failing-group-version-webhook" not found`, "Expected api retrieval error")
 	})
 
 	logger.Section("delete app that uses failing group version", func() {
diff --git a/test/e2e/kapp.go b/test/e2e/kapp.go
index cb6ce7a28..35097ad0a 100644
--- a/test/e2e/kapp.go
+++ b/test/e2e/kapp.go
@@ -6,12 +6,13 @@ package e2e
 import (
 	"bytes"
 	"fmt"
-	"github.com/stretchr/testify/require"
 	"io"
 	"os"
 	"os/exec"
 	"strings"
 	"testing"
+
+	"github.com/stretchr/testify/require"
 )
 
 type Kapp struct {
diff --git a/test/e2e/kubectl.go b/test/e2e/kubectl.go
index 048dd24ab..9bb992596 100644
--- a/test/e2e/kubectl.go
+++ b/test/e2e/kubectl.go
@@ -6,11 +6,12 @@ package e2e
 import (
 	"bytes"
 	"fmt"
-	"github.com/stretchr/testify/require"
 	"os"
 	"os/exec"
 	"strings"
 	"testing"
+
+	"github.com/stretchr/testify/require"
 )
 
 type Kubectl struct {
diff --git a/test/e2e/order_test.go b/test/e2e/order_test.go
index 4d0bf267e..661c08481 100644
--- a/test/e2e/order_test.go
+++ b/test/e2e/order_test.go
@@ -4,11 +4,12 @@
 package e2e
 
 import (
-	"github.com/stretchr/testify/require"
 	"regexp"
 	"sort"
 	"strings"
 	"testing"
+
+	"github.com/stretchr/testify/require"
 )
 
 func TestOrder(t *testing.T) {
diff --git a/test/e2e/update_replace_test.go b/test/e2e/update_replace_test.go
index 248d4927b..ceabc3f57 100644
--- a/test/e2e/update_replace_test.go
+++ b/test/e2e/update_replace_test.go
@@ -4,9 +4,10 @@
 package e2e
 
 import (
-	"github.com/stretchr/testify/require"
 	"strings"
 	"testing"
+
+	"github.com/stretchr/testify/require"
 )
 
 func TestUpdateFallbackOnReplace(t *testing.T) {
diff --git a/test/e2e/update_retry_on_conflict_test.go b/test/e2e/update_retry_on_conflict_test.go
index 9c79939b0..af16b5d48 100644
--- a/test/e2e/update_retry_on_conflict_test.go
+++ b/test/e2e/update_retry_on_conflict_test.go
@@ -183,7 +183,6 @@ spec:
 		_, err := kapp.RunWithOpts([]string{"deploy", "--tty", "-f", tmpFile.Name(), "-a", name},
 			RunOpts{IntoNs: true, StdinReader: promptOutput.YesReader(),
 				StdoutWriter: promptOutput.OutputWriter(), Interactive: true, AllowError: true})
-
 		require.Errorf(t, err, "Expected error, but err was nil")
 
 		require.Contains(t, err.Error(), "Failed to update due to resource conflict (approved diff no longer matches)",
@@ -312,7 +311,8 @@ func (p promptOutput) WaitPresented() {
 			break
 		}
 	}
-	require.NoError(p.t, scanner.Err())
+	err := scanner.Err()
+	require.NoError(p.t, err)
 }
 
 func newTmpFile(content string, t *testing.T) *os.File {