diff --git a/src/cmd/root.go b/src/cmd/root.go
index 876efdf20e..62e0582c8e 100644
--- a/src/cmd/root.go
+++ b/src/cmd/root.go
@@ -96,7 +96,8 @@ func Execute(ctx context.Context) {
 	if len(comps) > 1 && comps[1] == "tools" && slices.Contains(defaultPrintCmds, comps[2]) {
 		cmd.PrintErrln(cmd.ErrPrefix(), err.Error())
 	} else {
-		pterm.Error.Println(err.Error())
+		errParagraph := message.Paragraph(err.Error())
+		pterm.Error.Println(errParagraph)
 	}
 	os.Exit(1)
 }
diff --git a/src/internal/packager/helm/chart.go b/src/internal/packager/helm/chart.go
index 134bb4c493..daf59902e5 100644
--- a/src/internal/packager/helm/chart.go
+++ b/src/internal/packager/helm/chart.go
@@ -91,6 +91,9 @@ func (h *Helm) InstallOrUpgradeChart(ctx context.Context) (types.ConnectStrings,
 		return nil
 	}, retry.Context(ctx), retry.Attempts(uint(h.retries)), retry.Delay(500*time.Millisecond))
 	if err != nil {
+		removeMsg := "if you need to remove the failed chart, use `zarf package remove`"
+		installErr := fmt.Errorf("unable to install chart after %d attempts: %w: %s", h.retries, err, removeMsg)
+
 		releases, _ := histClient.Run(h.chart.ReleaseName)
 		previouslyDeployedVersion := 0
 
@@ -101,21 +104,18 @@ func (h *Helm) InstallOrUpgradeChart(ctx context.Context) (types.ConnectStrings,
 			}
 		}
 
-		removeMsg := "if you need to remove the failed chart, use `zarf package remove`"
-
 		// No prior releases means this was an initial install.
 		if previouslyDeployedVersion == 0 {
-			return nil, "", fmt.Errorf("unable to install chart after %d attempts: %s", h.retries, removeMsg)
+			return nil, "", installErr
 		}
 
 		// Attempt to rollback on a failed upgrade.
 		spinner.Updatef("Performing chart rollback")
 		err = h.rollbackChart(h.chart.ReleaseName, previouslyDeployedVersion)
 		if err != nil {
-			return nil, "", fmt.Errorf("unable to upgrade chart after %d attempts and unable to rollback: %s", h.retries, removeMsg)
+			return nil, "", fmt.Errorf("%w: unable to rollback: %w", installErr, err)
 		}
-
-		return nil, "", fmt.Errorf("unable to upgrade chart after %d attempts: %s", h.retries, removeMsg)
+		return nil, "", installErr
 	}
 
 	// return any collected connect strings for zarf connect.
diff --git a/src/test/e2e/09_component_compose_test.go b/src/test/e2e/09_component_compose_test.go
index 37a905456a..e5809df6eb 100644
--- a/src/test/e2e/09_component_compose_test.go
+++ b/src/test/e2e/09_component_compose_test.go
@@ -185,7 +185,7 @@ func (suite *CompositionSuite) Test_2_ComposabilityBadLocalOS() {
 
 	_, stdErr, err := e2e.Zarf(suite.T(), "package", "create", composeTestBadLocalOS, "-o", "build", "--no-color", "--confirm")
 	suite.Error(err)
-	suite.Contains(stdErr, "\"only.localOS\" \"linux\" cannot be redefined as \"windows\" during compose")
+	suite.Contains(e2e.StripMessageFormatting(stdErr), "\"only.localOS\" \"linux\" cannot be redefined as \"windows\" during compose")
 }
 
 func TestCompositionSuite(t *testing.T) {
diff --git a/src/test/e2e/20_zarf_init_test.go b/src/test/e2e/20_zarf_init_test.go
index 6f788ef3b1..c94bfa4226 100644
--- a/src/test/e2e/20_zarf_init_test.go
+++ b/src/test/e2e/20_zarf_init_test.go
@@ -44,7 +44,7 @@ func TestZarfInit(t *testing.T) {
 		// We need to use the --architecture flag here to force zarf to find the package.
 		_, stdErr, err = e2e.Zarf(t, "init", "--architecture", mismatchedArch, "--components=k3s", "--confirm")
 		require.Error(t, err, stdErr)
-		require.Contains(t, stdErr, expectedErrorMessage)
+		require.Contains(t, e2e.StripMessageFormatting(stdErr), expectedErrorMessage)
 	}
 
 	if !e2e.ApplianceMode {
diff --git a/src/test/e2e/31_checksum_and_signature_test.go b/src/test/e2e/31_checksum_and_signature_test.go
index e8aed4c1cb..b80e83e699 100644
--- a/src/test/e2e/31_checksum_and_signature_test.go
+++ b/src/test/e2e/31_checksum_and_signature_test.go
@@ -37,7 +37,7 @@ func TestChecksumAndSignature(t *testing.T) {
 	// Test that we get an error when trying to deploy a package without providing the public key
 	stdOut, stdErr, err = e2e.Zarf(t, "package", "deploy", pkgName, "--confirm")
 	require.Error(t, err, stdOut, stdErr)
-	require.Contains(t, stdErr, "failed to deploy package: unable to load the package: package is signed but no key was provided - add a key with the --key flag or use the --insecure flag and run the command again")
+	require.Contains(t, e2e.StripMessageFormatting(stdErr), "failed to deploy package: unable to load the package: package is signed but no key was provided - add a key with the --key flag or use the --insecure flag and run the command again")
 
 	// Test that we don't get an error when we remember to provide the public key
 	stdOut, stdErr, err = e2e.Zarf(t, "package", "deploy", pkgName, publicKeyFlag, "--confirm")
diff --git a/src/test/e2e/34_custom_init_package_test.go b/src/test/e2e/34_custom_init_package_test.go
index c61cf91e2d..e4d3307fc4 100644
--- a/src/test/e2e/34_custom_init_package_test.go
+++ b/src/test/e2e/34_custom_init_package_test.go
@@ -38,7 +38,7 @@ func TestCustomInit(t *testing.T) {
 	// Test that we get an error when trying to deploy a package without providing the public key
 	stdOut, stdErr, err = e2e.Zarf(t, "init", "--confirm")
 	require.Error(t, err, stdOut, stdErr)
-	require.Contains(t, stdErr, "unable to load the package: package is signed but no key was provided - add a key with the --key flag or use the --insecure flag and run the command again")
+	require.Contains(t, e2e.StripMessageFormatting(stdErr), "unable to load the package: package is signed but no key was provided - add a key with the --key flag or use the --insecure flag and run the command again")
 
 	/* Test operations during package deploy */
 	// Test that we can deploy the package with the public key