diff --git a/src/cmd/create.go b/src/cmd/create.go
index 531721b60..6de0ac4b0 100644
--- a/src/cmd/create.go
+++ b/src/cmd/create.go
@@ -241,6 +241,18 @@ func createContainer(container, image, release, authFile string, showCommandToEn
 		}
 	}
 
+	isImageCompatible, warningMessage, err := podman.DoesImageFulfillRequirements(imageFull)
+	if err != nil {
+		return fmt.Errorf("%w", err)
+	}
+
+	if !isImageCompatible {
+		fmt.Fprintf(os.Stderr, "%s\n", warningMessage)
+		if !rootFlags.assumeYes && !askForConfirmation("One or more of the image's requirements are not met. Continue anyway? [y/N]:") {
+			return nil
+		}
+	}
+
 	var toolbxDelayEntryPointEnv []string
 
 	if toolbxDelayEntryPoint, ok := os.LookupEnv("TOOLBX_DELAY_ENTRY_POINT"); ok {
diff --git a/src/cmd/rmi.go b/src/cmd/rmi.go
index f10b33da2..50bcffef3 100644
--- a/src/cmd/rmi.go
+++ b/src/cmd/rmi.go
@@ -90,9 +90,12 @@ func rmi(cmd *cobra.Command, args []string) error {
 		}
 
 		for _, image := range args {
-			if _, err := podman.IsToolboxImage(image); err != nil {
+			if isToolboxImage, err := podman.IsToolboxImage(image); err != nil {
 				fmt.Fprintf(os.Stderr, "Error: %s\n", err)
 				continue
+			} else if !isToolboxImage {
+				fmt.Fprintf(os.Stderr, "Error: %s is not a Toolbx image\n", image)
+				continue
 			}
 
 			if err := podman.RemoveImage(image, rmiFlags.forceDelete); err != nil {
diff --git a/src/cmd/run.go b/src/cmd/run.go
index 389ea1615..fbc04e034 100644
--- a/src/cmd/run.go
+++ b/src/cmd/run.go
@@ -183,6 +183,8 @@ func runCommand(container string,
 		}
 	}
 
+	checkImageCompatibility := true
+
 	logrus.Debugf("Checking if container %s exists", container)
 
 	if _, err := podman.ContainerExists(container); err != nil {
@@ -225,6 +227,10 @@ func runCommand(container string,
 			if err := createContainer(container, image, release, "", false); err != nil {
 				return err
 			}
+
+			// set to false -> check was already made when creating container during toolbx enter
+			checkImageCompatibility = false
+
 		} else if containersCount == 1 && defaultContainer {
 			fmt.Fprintf(os.Stderr, "Error: container %s not found\n", container)
 
@@ -249,6 +255,18 @@ func runCommand(container string,
 		return fmt.Errorf("failed to inspect container %s", container)
 	}
 
+	isImageCompatible, warningMessage, err := podman.DoesImageFulfillRequirements(containerObj.Image())
+	if err != nil {
+		return fmt.Errorf("%w", err)
+	}
+
+	if !isImageCompatible && checkImageCompatibility {
+		fmt.Fprintf(os.Stderr, "%s\n", warningMessage)
+		if !rootFlags.assumeYes && !askForConfirmation("One or more of the image's requirements are not met. Continue anyway? [y/N]:") {
+			return nil
+		}
+	}
+
 	entryPoint := containerObj.EntryPoint()
 	entryPointPID := containerObj.EntryPointPID()
 	logrus.Debugf("Entry point of container %s is %s (PID=%d)", container, entryPoint, entryPointPID)
diff --git a/src/pkg/podman/podman.go b/src/pkg/podman/podman.go
index 4711b8b5c..643b4bbad 100644
--- a/src/pkg/podman/podman.go
+++ b/src/pkg/podman/podman.go
@@ -24,6 +24,7 @@ import (
 	"fmt"
 	"io"
 	"strconv"
+	"strings"
 	"time"
 
 	"github.com/HarryMichal/go-version"
@@ -352,17 +353,84 @@ func IsToolboxImage(image string) (bool, error) {
 	}
 
 	if info["Labels"] == nil {
-		return false, fmt.Errorf("%s is not a Toolbx image", image)
+		return false, nil
 	}
 
 	labels := info["Labels"].(map[string]interface{})
 	if labels["com.github.containers.toolbox"] != "true" && labels["com.github.debarshiray.toolbox"] != "true" {
-		return false, fmt.Errorf("%s is not a Toolbx image", image)
+		return false, nil
 	}
 
 	return true, nil
 }
 
+func IsLDPRELOADEnvSet(image string) (bool, error) {
+	info, err := InspectImage(image)
+	if err != nil {
+		return false, fmt.Errorf("failed to inspect image %s: %s", image, err)
+	}
+
+	if info["Config"] == nil {
+		return false, nil
+	}
+
+	config := info["Config"].(map[string]interface{})
+	if config["Env"] == nil {
+		return false, nil
+	}
+
+	env := config["Env"]
+	switch envVars := env.(type) {
+	case []interface{}:
+		for _, envVar := range envVars {
+			if envVarStr, ok := envVar.(string); ok {
+				envVarStrTrimmed := strings.TrimSpace(envVarStr)
+				if strings.HasPrefix(envVarStrTrimmed, "LD_PRELOAD=") {
+					return true, nil
+				}
+			}
+		}
+	case []string:
+		for _, envVar := range envVars {
+			envVarTrimmed := strings.TrimSpace(envVar)
+			if strings.HasPrefix(envVarTrimmed, "LD_PRELOAD=") {
+				return true, nil
+			}
+		}
+	default:
+		return false, fmt.Errorf("unexpected type '%T' of environment variables in image %s", env, image)
+	}
+
+	return false, nil
+}
+
+func HasImageEntrypoint(image string) (bool, error) {
+	info, err := InspectImage(image)
+	if err != nil {
+		return false, fmt.Errorf("failed to inspect image %s: %s", image, err)
+	}
+
+	if info["Config"] == nil {
+		return false, nil
+	}
+
+	config := info["Config"].(map[string]interface{})
+	if config["Entrypoint"] == nil {
+		return false, nil
+	}
+
+	entrypoint := config["Entrypoint"]
+
+	switch ep := entrypoint.(type) {
+	case []interface{}:
+		return len(ep) > 0, nil
+	case []string:
+		return len(ep) > 0, nil
+	default:
+		return false, fmt.Errorf("unexpected type '%T' of entrypoint of image %s", entrypoint, image)
+	}
+}
+
 func Logs(container string, since time.Time, stderr io.Writer) error {
 	ctx := context.Background()
 	err := LogsContext(ctx, container, false, since, stderr)
@@ -506,3 +574,38 @@ func SystemMigrate(ociRuntimeRequired string) error {
 
 	return nil
 }
+
+func DoesImageFulfillRequirements(image string) (bool, string, error) {
+	var warnings []string
+
+	isToolboxImage, err := IsToolboxImage(image)
+	if err != nil {
+		return false, "", fmt.Errorf("failed to verify image compatibility: %w", err)
+	}
+	if !isToolboxImage {
+		warnings = append(warnings, fmt.Sprintf("Warning: Image '%s' does not contain either of the labels 'com.github.containers.toolbox=true' and 'com.github.debarshiray.toolbox=true'", image))
+	}
+
+	isLDPRELOADEnvSet, err := IsLDPRELOADEnvSet(image)
+	if err != nil {
+		return false, "", fmt.Errorf("failed to validate LD_PRELOAD variable settings: %w", err)
+	}
+	if isLDPRELOADEnvSet {
+		warnings = append(warnings, fmt.Sprintf("Warning: Image '%s' has environment variable LD_PRELOAD set, which may cause container vulnerability (Container Escape)", image))
+	}
+
+	hasEntrypoint, err := HasImageEntrypoint(image)
+	if err != nil {
+		return false, "", fmt.Errorf("failed to check image entrypoint: %w", err)
+	}
+	if hasEntrypoint {
+		warnings = append(warnings, fmt.Sprintf("Warning: Image '%s' has an entrypoint defined", image))
+	}
+
+	if len(warnings) > 0 {
+		warningMessage := strings.Join(warnings, "\n")
+		return false, warningMessage, nil
+	}
+
+	return true, "", nil
+}
diff --git a/test/system/101-create.bats b/test/system/101-create.bats
index db7c7651e..a2d99a1fc 100644
--- a/test/system/101-create.bats
+++ b/test/system/101-create.bats
@@ -1009,3 +1009,257 @@ teardown() {
   assert [ ${#lines[@]} -eq 2 ]
   assert [ ${#stderr_lines[@]} -eq 0 ]
 }
+
+@test "create: With a non-Toolbx image and prompt for confirmation - Yes" {
+  image="$(build_non_toolbx_image)"
+  containerName="test-container-non-toolbx"
+
+  run --keep-empty-lines --separate-stderr "$TOOLBX" create --image "$image" "$containerName" <<< "y"
+
+  assert_success
+  assert_line --index 0 "${MSG_CONFIRMATION_PROMPT}$(created_container_message "$containerName")"
+  assert_line --index 1 "$(enter_with_message "$containerName")"
+  assert [ ${#lines[@]} -eq 2 ]
+
+  lines=("${stderr_lines[@]}")
+  assert_line --index 0 "$(warning_non_toolbx_image "$image")"
+  assert [ ${#stderr_lines[@]} -eq 1 ]
+
+  run podman ps --all
+
+  assert_success
+  assert_output --regexp "Created[[:blank:]]+$containerName"
+}
+
+@test "create: With a non-Toolbx image and prompt for confirmation - No" {
+  image="$(build_non_toolbx_image)"
+  containerName="test-container-non-toolbx"
+
+  run --keep-empty-lines --separate-stderr "$TOOLBX" create --image "$image" "$containerName" <<< "n"
+
+  assert_success
+  assert_line --index 0 "${MSG_CONFIRMATION_PROMPT}"
+  assert [ ${#lines[@]} -eq 1 ]
+
+  lines=("${stderr_lines[@]}")
+  assert_line --index 0 "$(warning_non_toolbx_image "$image")"
+  assert [ ${#stderr_lines[@]} -eq 1 ]
+
+  run podman ps --all
+
+  assert_success
+  assert [ ${#lines[@]} -eq 1 ]
+}
+
+@test "create: With a non-Toolbx image and prompt for confirmation - assumeyes" {
+  image="$(build_non_toolbx_image)"
+  containerName="test-container-non-toolbx"
+
+  run --keep-empty-lines --separate-stderr "$TOOLBX" create --assumeyes --image "$image" "$containerName"
+
+  assert_success
+  assert_line --index 0 "$(created_container_message "$containerName")"
+  assert_line --index 1 "$(enter_with_message "$containerName")"
+  assert [ ${#lines[@]} -eq 2 ]
+
+  lines=("${stderr_lines[@]}")
+  assert_line --index 0 "$(warning_non_toolbx_image "$image")"
+  assert [ ${#stderr_lines[@]} -eq 1 ]
+
+  run podman ps --all
+
+  assert_success
+  assert_output --regexp "Created[[:blank:]]+$containerName"
+}
+
+@test "create: With an image with LD_PRELOAD set and prompt for confirmation - Yes" {
+  containerName="test-container-ld-preload"
+  image="$(build_image_with_ld_preload)"
+
+  run --keep-empty-lines --separate-stderr "$TOOLBX" create --image "$image" "$containerName" <<< "y"
+
+  assert_success
+  assert_line --index 0 "${MSG_CONFIRMATION_PROMPT}$(created_container_message "$containerName")"
+  assert_line --index 1 "$(enter_with_message "$containerName")"
+  assert [ ${#lines[@]} -eq 2 ]
+
+  lines=("${stderr_lines[@]}")
+  assert_line --index 0 "$(warning_ld_preload_image "$image")"
+  assert [ ${#stderr_lines[@]} -eq 1 ]
+
+  run podman ps --all
+
+  assert_success
+  assert_output --regexp "Created[[:blank:]]+$containerName"
+}
+
+@test "create: With an image with LD_PRELOAD set and prompt for confirmation - No" {
+  containerName="test-container-ld-preload"
+  image="$(build_image_with_ld_preload)"
+
+  run --keep-empty-lines --separate-stderr "$TOOLBX" create --image "$image" "$containerName" <<< "n"
+
+  assert_success
+  assert_line --index 0 "${MSG_CONFIRMATION_PROMPT}"
+  assert [ ${#lines[@]} -eq 1 ]
+
+  lines=("${stderr_lines[@]}")
+  assert_line --index 0 "$(warning_ld_preload_image "$image")"
+  assert [ ${#stderr_lines[@]} -eq 1 ]
+
+  run podman ps --all
+
+  assert_success
+  assert [ ${#lines[@]} -eq 1 ]
+}
+
+@test "create: With an image with LD_PRELOAD set and prompt for confirmation - assumeyes" {
+  containerName="test-container-ld-preload"
+  image="$(build_image_with_ld_preload)"
+
+  run --keep-empty-lines --separate-stderr "$TOOLBX" --assumeyes create --image "$image" "$containerName"
+
+  assert_success
+  assert_line --index 0 "$(created_container_message "$containerName")"
+  assert_line --index 1 "$(enter_with_message "$containerName")"
+  assert [ ${#lines[@]} -eq 2 ]
+
+  lines=("${stderr_lines[@]}")
+  assert_line --index 0 "$(warning_ld_preload_image "$image")"
+  assert [ ${#stderr_lines[@]} -eq 1 ]
+
+  run podman ps --all
+
+  assert_success
+  assert_output --regexp "Created[[:blank:]]+$containerName"
+}
+
+@test "create: With an image with an entrypoint set and prompt for confirmation - Yes" {
+  containerName="test-container-entrypoint"
+  image="$(build_image_with_entrypoint)"
+
+  run --keep-empty-lines --separate-stderr "$TOOLBX" create --image "$image" "$containerName" <<< "y"
+
+  assert_success
+  assert_line --index 0 "${MSG_CONFIRMATION_PROMPT}$(created_container_message "$containerName")"
+  assert_line --index 1 "$(enter_with_message "$containerName")"
+  assert [ ${#lines[@]} -eq 2 ]
+
+  lines=("${stderr_lines[@]}")
+  assert_line --index 0 "$(warning_entrypoint_image "$image")"
+  assert [ ${#stderr_lines[@]} -eq 1 ]
+
+  run podman ps --all
+
+  assert_success
+  assert_output --regexp "Created[[:blank:]]+$containerName"
+}
+
+@test "create: With an image with an entrypoint set and prompt for confirmation - No" {
+  containerName="test-container-entrypoint"
+  image="$(build_image_with_entrypoint)"
+
+  run --keep-empty-lines --separate-stderr "$TOOLBX" create --image "$image" "$containerName" <<< "n"
+
+  assert_success
+  assert_line --index 0 "${MSG_CONFIRMATION_PROMPT}"
+  assert [ ${#lines[@]} -eq 1 ]
+
+  lines=("${stderr_lines[@]}")
+  assert_line --index 0 "$(warning_entrypoint_image "$image")"
+  assert [ ${#stderr_lines[@]} -eq 1 ]
+
+  run podman ps --all
+
+  assert_success
+  assert [ ${#lines[@]} -eq 1 ]
+}
+
+@test "create: With an image with an entrypoint set and prompt for confirmation - assumeyes" {
+  containerName="test-container-entrypoint"
+  image="$(build_image_with_entrypoint)"
+
+  run --keep-empty-lines --separate-stderr "$TOOLBX" --assumeyes create --image "$image" "$containerName"
+
+  assert_success
+  assert_line --index 0 "$(created_container_message "$containerName")"
+  assert_line --index 1 "$(enter_with_message "$containerName")"
+  assert [ ${#lines[@]} -eq 2 ]
+
+  lines=("${stderr_lines[@]}")
+  assert_line --index 0 "$(warning_entrypoint_image "$image")"
+  assert [ ${#stderr_lines[@]} -eq 1 ]
+
+  run podman ps --all
+
+  assert_success
+  assert_output --regexp "Created[[:blank:]]+$containerName"
+}
+
+@test "create: With an image having all warnings and prompt for confirmation - Yes" {
+  containerName="test-container-all-warnings"
+  image="$(build_image_with_all_warnings)"
+
+  run --keep-empty-lines --separate-stderr "$TOOLBX" create --image "$image" "$containerName" <<< "y"
+
+  assert_success
+  assert_line --index 0 "${MSG_CONFIRMATION_PROMPT}$(created_container_message "$containerName")"
+  assert_line --index 1 "$(enter_with_message "$containerName")"
+  assert [ ${#lines[@]} -eq 2 ]
+
+  lines=("${stderr_lines[@]}")
+  assert_line --index 0 "$(warning_non_toolbx_image "$image")"
+  assert_line --index 1 "$(warning_ld_preload_image "$image")"
+  assert_line --index 2 "$(warning_entrypoint_image "$image")"
+  assert [ ${#stderr_lines[@]} -eq 3 ]
+
+  run podman ps --all
+
+  assert_success
+  assert_output --regexp "Created[[:blank:]]+$containerName"
+}
+
+@test "create: With an image having all warnings and prompt for confirmation - No" {
+  containerName="test-container-all-warnings"
+  image="$(build_image_with_all_warnings)"
+
+  run --keep-empty-lines --separate-stderr "$TOOLBX" create --image "$image" "$containerName" <<< "n"
+
+  assert_success
+  assert_line --index 0 "${MSG_CONFIRMATION_PROMPT}"
+  assert [ ${#lines[@]} -eq 1 ]
+
+  lines=("${stderr_lines[@]}")
+  assert_line --index 0 "$(warning_non_toolbx_image "$image")"
+  assert_line --index 1 "$(warning_ld_preload_image "$image")"
+  assert_line --index 2 "$(warning_entrypoint_image "$image")"
+  assert [ ${#stderr_lines[@]} -eq 3 ]
+
+  run podman ps --all
+
+  assert_success
+  assert [ ${#lines[@]} -eq 1 ]
+}
+
+@test "create: With an image having all warnings and prompt for confirmation - assumeyes" {
+  containerName="test-container-all-warnings"
+  image="$(build_image_with_all_warnings)"
+
+  run --keep-empty-lines --separate-stderr "$TOOLBX" create --assumeyes --image "$image" "$containerName"
+
+  assert_success
+  assert_line --index 0 "$(created_container_message "$containerName")"
+  assert_line --index 1 "$(enter_with_message "$containerName")"
+  assert [ ${#lines[@]} -eq 2 ]
+
+  lines=("${stderr_lines[@]}")
+  assert_line --index 0 "$(warning_non_toolbx_image "$image")"
+  assert_line --index 1 "$(warning_ld_preload_image "$image")"
+  assert_line --index 2 "$(warning_entrypoint_image "$image")"
+  assert [ ${#stderr_lines[@]} -eq 3 ]
+
+  run podman ps --all
+
+  assert_success
+  assert_output --regexp "Created[[:blank:]]+$containerName"
+}
diff --git a/test/system/104-run.bats b/test/system/104-run.bats
index 3883deeb5..245481d97 100644
--- a/test/system/104-run.bats
+++ b/test/system/104-run.bats
@@ -863,3 +863,217 @@ teardown() {
   assert_line --index 1 "Recreate it with Toolbx version 0.0.17 or newer."
   assert [ ${#stderr_lines[@]} -eq 2 ]
 }
+
+@test "run: With a non-Toolbx image and prompt for confirmation - Yes" {
+  containerName="test-container-non-toolbx"
+  image="$(build_non_toolbx_image)"
+
+  create_image_container "$image" "$containerName"
+
+  run --keep-empty-lines --separate-stderr "$TOOLBX" run --container "$containerName" true <<< "y"
+
+  assert_failure
+  assert_line --index 0 "${MSG_CONFIRMATION_PROMPT}"
+  assert [ ${#lines[@]} -eq 1 ]
+
+  lines=("${stderr_lines[@]}")
+  assert_line --index 0 "$(warning_non_toolbx_image "$image")"
+  assert_line --index 1 "$(failed_start_error_message "$containerName")"
+  assert [ ${#stderr_lines[@]} -eq 2 ]
+}
+
+@test "run: With a non-Toolbx image and prompt for confirmation - No" {
+  containerName="test-container-non-toolbx"
+  image="$(build_non_toolbx_image)"
+
+  create_image_container "$image" "$containerName"
+
+  run --keep-empty-lines --separate-stderr "$TOOLBX" run --container "$containerName" true <<< "n"
+
+  assert_success
+  assert_line --index 0 "${MSG_CONFIRMATION_PROMPT}"
+  assert [ ${#lines[@]} -eq 1 ]
+
+  lines=("${stderr_lines[@]}")
+  assert_line --index 0 "$(warning_non_toolbx_image "$image")"
+  assert [ ${#stderr_lines[@]} -eq 1 ]
+}
+
+@test "run: With a non-Toolbx image and prompt for confirmation - assumeyes" {
+  containerName="test-container-non-toolbx"
+  image="$(build_non_toolbx_image)"
+
+  create_image_container "$image" "$containerName"
+
+  run --keep-empty-lines --separate-stderr "$TOOLBX" --assumeyes run --container "$containerName" true
+
+  assert_failure
+  assert [ ${#lines[@]} -eq 0 ]
+
+  lines=("${stderr_lines[@]}")
+  assert_line --index 0 "$(warning_non_toolbx_image "$image")"
+  assert_line --index 1 "$(failed_start_error_message "$containerName")"
+  assert [ ${#stderr_lines[@]} -eq 2 ]
+}
+
+@test "run: With an image with LD_PRELOAD set and prompt for confirmation - Yes" {
+  containerName="test-container-ld-preload"
+  image="$(build_image_with_ld_preload)"
+
+  create_image_container "$image" "$containerName"
+
+  run --keep-empty-lines --separate-stderr "$TOOLBX" run --container "$containerName" true <<< "y"
+
+  assert_failure
+  assert_line --index 0 "${MSG_CONFIRMATION_PROMPT}"
+  assert [ ${#lines[@]} -eq 1 ]
+
+  lines=("${stderr_lines[@]}")
+  assert_line --index 0 "$(warning_ld_preload_image "$image")"
+  assert_line --index 1 "$(failed_start_error_message "$containerName")"
+  assert [ ${#stderr_lines[@]} -eq 2 ]
+}
+
+@test "run: With an image with LD_PRELOAD set and prompt for confirmation - No" {
+  containerName="test-container-ld-preload"
+  image="$(build_image_with_ld_preload)"
+
+  create_image_container "$image" "$containerName"
+
+  run --keep-empty-lines --separate-stderr "$TOOLBX" run --container "$containerName" true <<< "n"
+
+  assert_success
+  assert_line --index 0 "${MSG_CONFIRMATION_PROMPT}"
+  assert [ ${#lines[@]} -eq 1 ]
+
+  lines=("${stderr_lines[@]}")
+  assert_line --index 0 "$(warning_ld_preload_image "$image")"
+  assert [ ${#stderr_lines[@]} -eq 1 ]
+}
+
+@test "run: With an image with LD_PRELOAD set and prompt for confirmation - assumeyes" {
+  containerName="test-container-ld-preload"
+  image="$(build_image_with_ld_preload)"
+
+  create_image_container "$image" "$containerName"
+
+  run --keep-empty-lines --separate-stderr "$TOOLBX" --assumeyes run --container "$containerName" true
+
+  assert_failure
+  assert [ ${#lines[@]} -eq 0 ]
+
+  lines=("${stderr_lines[@]}")
+  assert_line --index 0 "$(warning_ld_preload_image "$image")"
+  assert_line --index 1 "$(failed_start_error_message "$containerName")"
+  assert [ ${#stderr_lines[@]} -eq 2 ]
+}
+
+@test "run: With an image with an entrypoint set and prompt for confirmation - Yes" {
+  containerName="test-container-entrypoint"
+  image="$(build_image_with_entrypoint)"
+
+  create_image_container "$image" "$containerName"
+
+  run --keep-empty-lines --separate-stderr "$TOOLBX" run --container "$containerName" true <<< "y"
+
+  assert_failure
+  assert_line --index 0 "${MSG_CONFIRMATION_PROMPT}"
+  assert [ ${#lines[@]} -eq 1 ]
+
+  lines=("${stderr_lines[@]}")
+  assert_line --index 0 "$(warning_entrypoint_image "$image")"
+  assert_line --index 1 "$(failed_start_error_message "$containerName")"
+  assert [ ${#stderr_lines[@]} -eq 2 ]
+}
+
+@test "run: With an image with an entrypoint set and prompt for confirmation - No" {
+  containerName="test-container-entrypoint"
+  image="$(build_image_with_entrypoint)"
+
+  create_image_container "$image" "$containerName"
+
+  run --keep-empty-lines --separate-stderr "$TOOLBX" run --container "$containerName" true <<< "n"
+
+  assert_success
+  assert_line --index 0 "${MSG_CONFIRMATION_PROMPT}"
+  assert [ ${#lines[@]} -eq 1 ]
+
+  lines=("${stderr_lines[@]}")
+  assert_line --index 0 "$(warning_entrypoint_image "$image")"
+  assert [ ${#stderr_lines[@]} -eq 1 ]
+}
+
+@test "run: With an image with an entrypoint set and prompt for confirmation - assumeyes" {
+  containerName="test-container-entrypoint"
+  image="$(build_image_with_entrypoint)"
+
+  create_image_container "$image" "$containerName"
+
+  run --keep-empty-lines --separate-stderr "$TOOLBX" --assumeyes run --container "$containerName" true
+
+  assert_failure
+  assert [ ${#lines[@]} -eq 0 ]
+
+  lines=("${stderr_lines[@]}")
+  assert_line --index 0 "$(warning_entrypoint_image "$image")"
+  assert_line --index 1 "$(failed_start_error_message "$containerName")"
+  assert [ ${#stderr_lines[@]} -eq 2 ]
+}
+
+@test "run: With an image having all warnings and prompt for confirmation - Yes" {
+  containerName="test-container-all-warnings"
+  image="$(build_image_with_all_warnings)"
+
+  create_image_container "$image" "$containerName"
+
+  run --keep-empty-lines --separate-stderr "$TOOLBX" run --container "$containerName" true <<< "y"
+
+  assert_failure
+  assert_line --index 0 "${MSG_CONFIRMATION_PROMPT}"
+  assert [ ${#lines[@]} -eq 1 ]
+
+  lines=("${stderr_lines[@]}")
+  assert_line --index 0 "$(warning_non_toolbx_image "$image")"
+  assert_line --index 1 "$(warning_ld_preload_image "$image")"
+  assert_line --index 2 "$(warning_entrypoint_image "$image")"
+  assert_line --index 3 "$(failed_start_error_message "$containerName")"
+  assert [ ${#stderr_lines[@]} -eq 4 ]
+}
+
+@test "run: With an image having all warnings and prompt for confirmation - No" {
+  containerName="test-container-all-warnings"
+  image="$(build_image_with_all_warnings)"
+
+  create_image_container "$image" "$containerName"
+
+  run --keep-empty-lines --separate-stderr "$TOOLBX" run --container "$containerName" true <<< "n"
+
+  assert_success
+  assert_line --index 0 "${MSG_CONFIRMATION_PROMPT}"
+  assert [ ${#lines[@]} -eq 1 ]
+
+  lines=("${stderr_lines[@]}")
+  assert_line --index 0 "$(warning_non_toolbx_image "$image")"
+  assert_line --index 1 "$(warning_ld_preload_image "$image")"
+  assert_line --index 2 "$(warning_entrypoint_image "$image")"
+  assert [ ${#stderr_lines[@]} -eq 3 ]
+}
+
+@test "run: With an image having all warnings and prompt for confirmation - assumeyes" {
+  containerName="test-container-all-warnings"
+  image="$(build_image_with_all_warnings)"
+
+  create_image_container "$image" "$containerName"
+
+  run --keep-empty-lines --separate-stderr "$TOOLBX" --assumeyes run --container "$containerName" true
+
+  assert_failure
+  assert [ ${#lines[@]} -eq 0 ]
+
+  lines=("${stderr_lines[@]}")
+  assert_line --index 0 "$(warning_non_toolbx_image "$image")"
+  assert_line --index 1 "$(warning_ld_preload_image "$image")"
+  assert_line --index 2 "$(warning_entrypoint_image "$image")"
+  assert_line --index 3 "$(failed_start_error_message "$containerName")"
+  assert [ ${#stderr_lines[@]} -eq 4 ]
+}
diff --git a/test/system/105-enter.bats b/test/system/105-enter.bats
index 6ff900e47..7eef5bc54 100644
--- a/test/system/105-enter.bats
+++ b/test/system/105-enter.bats
@@ -147,6 +147,220 @@ teardown() {
   assert [ ${#lines[@]} -eq 3 ]
 }
 
+@test "enter: With a non-Toolbx image and prompt for confirmation - Yes" {
+  containerName="test-container-non-toolbx"
+  image="$(build_non_toolbx_image)"
+
+  create_image_container "$image" "$containerName"
+
+  run --keep-empty-lines --separate-stderr "$TOOLBX" enter --container "$containerName" <<< "y"
+
+  assert_failure
+  assert_line --index 0 "${MSG_CONFIRMATION_PROMPT}"
+  assert [ ${#lines[@]} -eq 1 ]
+
+  lines=("${stderr_lines[@]}")
+  assert_line --index 0 "$(warning_non_toolbx_image "$image")"
+  assert_line --index 1 "$(failed_start_error_message "$containerName")"
+  assert [ ${#stderr_lines[@]} -eq 2 ]
+}
+
+@test "enter: With a non-Toolbx image and prompt for confirmation - No" {
+  containerName="test-container-non-toolbx"
+  image="$(build_non_toolbx_image)"
+
+  create_image_container "$image" "$containerName"
+
+  run --keep-empty-lines --separate-stderr "$TOOLBX" enter --container "$containerName" <<< "n"
+
+  assert_success
+  assert_line --index 0 "${MSG_CONFIRMATION_PROMPT}"
+  assert [ ${#lines[@]} -eq 1 ]
+
+  lines=("${stderr_lines[@]}")
+  assert_line --index 0 "$(warning_non_toolbx_image "$image")"
+  assert [ ${#stderr_lines[@]} -eq 1 ]
+}
+
+@test "enter: With a non-Toolbx image and prompt for confirmation - assumeyes" {
+  containerName="test-container-non-toolbx"
+  image="$(build_non_toolbx_image)"
+
+  create_image_container "$image" "$containerName"
+
+  run --keep-empty-lines --separate-stderr "$TOOLBX" --assumeyes enter --container "$containerName"
+
+  assert_failure
+  assert [ ${#lines[@]} -eq 0 ]
+
+  lines=("${stderr_lines[@]}")
+  assert_line --index 0 "$(warning_non_toolbx_image "$image")"
+  assert_line --index 1 "$(failed_start_error_message "$containerName")"
+  assert [ ${#stderr_lines[@]} -eq 2 ]
+}
+
+@test "enter: With an image with LD_PRELOAD set and prompt for confirmation - Yes" {
+  containerName="test-container-ld-preload"
+  image="$(build_image_with_ld_preload)"
+
+  create_image_container "$image" "$containerName"
+
+  run --keep-empty-lines --separate-stderr "$TOOLBX" enter --container "$containerName" <<< "y"
+
+  assert_failure
+  assert_line --index 0 "${MSG_CONFIRMATION_PROMPT}"
+  assert [ ${#lines[@]} -eq 1 ]
+
+  lines=("${stderr_lines[@]}")
+  assert_line --index 0 "$(warning_ld_preload_image "$image")"
+  assert_line --index 1 "$(failed_start_error_message "$containerName")"
+  assert [ ${#stderr_lines[@]} -eq 2 ]
+}
+
+@test "enter: With an image with LD_PRELOAD set and prompt for confirmation - No" {
+  containerName="test-container-ld-preload"
+  image="$(build_image_with_ld_preload)"
+
+  create_image_container "$image" "$containerName"
+
+  run --keep-empty-lines --separate-stderr "$TOOLBX" enter --container "$containerName" <<< "n"
+
+  assert_success
+  assert_line --index 0 "${MSG_CONFIRMATION_PROMPT}"
+  assert [ ${#lines[@]} -eq 1 ]
+
+  lines=("${stderr_lines[@]}")
+  assert_line --index 0 "$(warning_ld_preload_image "$image")"
+  assert [ ${#stderr_lines[@]} -eq 1 ]
+}
+
+@test "enter: With an image with LD_PRELOAD set and prompt for confirmation - assumeyes" {
+  containerName="test-container-ld-preload"
+  image="$(build_image_with_ld_preload)"
+
+  create_image_container "$image" "$containerName"
+
+  run --keep-empty-lines --separate-stderr "$TOOLBX" --assumeyes enter --container "$containerName"
+
+  assert_failure
+  assert [ ${#lines[@]} -eq 0 ]
+
+  lines=("${stderr_lines[@]}")
+  assert_line --index 0 "$(warning_ld_preload_image "$image")"
+  assert_line --index 1 "$(failed_start_error_message "$containerName")"
+  assert [ ${#stderr_lines[@]} -eq 2 ]
+}
+
+@test "enter: With an image with an entrypoint set and prompt for confirmation - Yes" {
+  containerName="test-container-entrypoint"
+  image="$(build_image_with_entrypoint)"
+
+  create_image_container "$image" "$containerName"
+
+  run --keep-empty-lines --separate-stderr "$TOOLBX" enter --container "$containerName" <<< "y"
+
+  assert_failure
+  assert_line --index 0 "${MSG_CONFIRMATION_PROMPT}"
+  assert [ ${#lines[@]} -eq 1 ]
+
+  lines=("${stderr_lines[@]}")
+  assert_line --index 0 "$(warning_entrypoint_image "$image")"
+  assert_line --index 1 "$(failed_start_error_message "$containerName")"
+  assert [ ${#stderr_lines[@]} -eq 2 ]
+}
+
+@test "enter: With an image with an entrypoint set and prompt for confirmation - No" {
+  containerName="test-container-entrypoint"
+  image="$(build_image_with_entrypoint)"
+
+  create_image_container "$image" "$containerName"
+
+  run --keep-empty-lines --separate-stderr "$TOOLBX" enter --container "$containerName" <<< "n"
+
+  assert_success
+  assert_line --index 0 "${MSG_CONFIRMATION_PROMPT}"
+  assert [ ${#lines[@]} -eq 1 ]
+
+  lines=("${stderr_lines[@]}")
+  assert_line --index 0 "$(warning_entrypoint_image "$image")"
+  assert [ ${#stderr_lines[@]} -eq 1 ]
+}
+
+@test "enter: With an image with an entrypoint set and prompt for confirmation - assumeyes" {
+  containerName="test-container-entrypoint"
+  image="$(build_image_with_entrypoint)"
+
+  create_image_container "$image" "$containerName"
+
+  run --keep-empty-lines --separate-stderr "$TOOLBX" --assumeyes enter --container "$containerName"
+
+  assert_failure
+  assert [ ${#lines[@]} -eq 0 ]
+
+  lines=("${stderr_lines[@]}")
+  assert_line --index 0 "$(warning_entrypoint_image "$image")"
+  assert_line --index 1 "$(failed_start_error_message "$containerName")"
+  assert [ ${#stderr_lines[@]} -eq 2 ]
+}
+
+@test "enter: With an image having all warnings and prompt for confirmation - Yes" {
+  containerName="test-container-all-warnings"
+  image="$(build_image_with_all_warnings)"
+
+  create_image_container "$image" "$containerName"
+
+  run --keep-empty-lines --separate-stderr "$TOOLBX" enter --container "$containerName" <<< "y"
+
+  assert_failure
+  assert_line --index 0 "${MSG_CONFIRMATION_PROMPT}"
+  assert [ ${#lines[@]} -eq 1 ]
+
+  lines=("${stderr_lines[@]}")
+  assert_line --index 0 "$(warning_non_toolbx_image "$image")"
+  assert_line --index 1 "$(warning_ld_preload_image "$image")"
+  assert_line --index 2 "$(warning_entrypoint_image "$image")"
+  assert_line --index 3 "$(failed_start_error_message "$containerName")"
+  assert [ ${#stderr_lines[@]} -eq 4 ]
+}
+
+@test "enter: With an image having all warnings and prompt for confirmation - No" {
+  containerName="test-container-all-warnings"
+  image="$(build_image_with_all_warnings)"
+
+  create_image_container "$image" "$containerName"
+
+  run --keep-empty-lines --separate-stderr "$TOOLBX" enter --container "$containerName" <<< "n"
+
+  assert_success
+  assert_line --index 0 "${MSG_CONFIRMATION_PROMPT}"
+  assert [ ${#lines[@]} -eq 1 ]
+
+  lines=("${stderr_lines[@]}")
+  assert_line --index 0 "$(warning_non_toolbx_image "$image")"
+  assert_line --index 1 "$(warning_ld_preload_image "$image")"
+  assert_line --index 2 "$(warning_entrypoint_image "$image")"
+  assert [ ${#stderr_lines[@]} -eq 3 ]
+}
+
+@test "enter: With an image having all warnings and prompt for confirmation - assumeyes" {
+  containerName="test-container-all-warnings"
+  image="$(build_image_with_all_warnings)"
+
+  create_image_container "$image" "$containerName"
+
+  run --keep-empty-lines --separate-stderr "$TOOLBX" --assumeyes enter --container "$containerName"
+
+  assert_failure
+  assert [ ${#lines[@]} -eq 0 ]
+
+  lines=("${stderr_lines[@]}")
+  assert_line --index 0 "$(warning_non_toolbx_image "$image")"
+  assert_line --index 1 "$(warning_ld_preload_image "$image")"
+  assert_line --index 2 "$(warning_entrypoint_image "$image")"
+  assert_line --index 3 "$(failed_start_error_message "$containerName")"
+  assert [ ${#stderr_lines[@]} -eq 4 ]
+}
+
 # TODO: Write the test
 @test "enter: Enter the default Toolbx" {
   skip "Testing of entering Toolbxes is not implemented"
diff --git a/test/system/libs/helpers.bash b/test/system/libs/helpers.bash
index 33b42eaf6..4ed593f3a 100644
--- a/test/system/libs/helpers.bash
+++ b/test/system/libs/helpers.bash
@@ -39,6 +39,42 @@ readonly TOOLBX="${TOOLBX:-$(command -v toolbox)}"
 readonly TOOLBX_TEST_SYSTEM_TAGS_ALL="arch-fedora,commands-options,custom-image,runtime-environment,ubuntu"
 readonly TOOLBX_TEST_SYSTEM_TAGS="${TOOLBX_TEST_SYSTEM_TAGS:-$TOOLBX_TEST_SYSTEM_TAGS_ALL}"
 
+
+# Common test messages (used across multiple test suites)
+export MSG_CONFIRMATION_PROMPT="One or more of the image's requirements are not met. Continue anyway? [y/N]: "
+
+# Helper functions for generating common messages
+function created_container_message() {
+  local container_name="$1"
+  echo "Created container: $container_name"
+}
+
+function enter_with_message() {
+  local container_name="$1"
+  echo "Enter with: toolbox enter $container_name"
+}
+
+function failed_start_error_message() {
+  local container_name="$1"
+  echo "Error: failed to start container $container_name"
+}
+
+# Helper functions for generating image warning messages
+function warning_non_toolbx_image() {
+  local image="$1"
+  echo "Warning: Image '$image' does not contain either of the labels 'com.github.containers.toolbox=true' and 'com.github.debarshiray.toolbox=true'"
+}
+
+function warning_ld_preload_image() {
+  local image="$1"
+  echo "Warning: Image '$image' has environment variable LD_PRELOAD set, which may cause container vulnerability (Container Escape)"
+}
+
+function warning_entrypoint_image() {
+  local image="$1"
+  echo "Warning: Image '$image' has an entrypoint defined"
+}
+
 # Images
 declare -Ag IMAGES=([arch]="quay.io/toolbx/arch-toolbox" \
                    [busybox]="quay.io/toolbox_tests/busybox" \
@@ -255,6 +291,57 @@ function build_image_without_name() {
 }
 
 
+# Generic helper function to build test images with custom Containerfile content
+#
+# Parameters
+# ==========
+# - image_name - Used as part of the image name
+# - containerfile_content - Complete Containerfile content to build the image
+#
+# The function creates a temporary Containerfile with the provided content,
+# builds the image using Podman, and returns the full image name that was built.
+function _build_test_image_generic() {
+  local image_name="$1"
+  local containerfile_content="$2"
+
+  local image_name_full="localhost/${image_name}:test-$$"
+
+  echo -e "$containerfile_content" > "$BATS_TEST_TMPDIR"/Containerfile
+
+  run podman build --quiet --tag "$image_name_full" "$BATS_TEST_TMPDIR"
+
+  assert_success
+  assert_line --index 0 --regexp "^[a-f0-9]{64}$"
+
+  # shellcheck disable=SC2154
+  assert [ ${#lines[@]} -eq 1 ]
+
+  rm -f "$BATS_TEST_TMPDIR"/Containerfile
+
+  echo "$image_name_full"
+}
+
+
+function build_non_toolbx_image() {
+  _build_test_image_generic "non-toolbx" "FROM scratch\n\nLABEL test=\"non-toolbx\""
+}
+
+
+function build_image_with_ld_preload() {
+  _build_test_image_generic "ld-preload" "FROM scratch\n\nENV LD_PRELOAD=foobar.so\n\nLABEL com.github.containers.toolbox=true"
+}
+
+
+function build_image_with_entrypoint() {
+  _build_test_image_generic "entrypoint" "FROM scratch\n\nENTRYPOINT [\"/bin/sh\", \"-c\", \"echo 'Hello, World!'\"]\n\nLABEL com.github.containers.toolbox=true"
+}
+
+
+function build_image_with_all_warnings() {
+  _build_test_image_generic "all-warnings" "FROM scratch\n\nENV LD_PRELOAD=foobar.so\n\nENTRYPOINT [\"/bin/sh\", \"-c\", \"echo 'Multiple warnings!'\"]\n\nLABEL test=\"all-warnings\""
+}
+
+
 function check_bats_version() {
     local required_version
     required_version="$1"
@@ -422,6 +509,24 @@ function create_default_container() {
 }
 
 
+# Creates a container with specific name and image
+#
+# Parameters:
+# ===========
+# - image - name of the image
+# - container_name - name of the container
+function create_image_container() {
+  local image
+  local container_name
+
+  image="$1"
+  container_name="$2"
+
+  "$TOOLBX" --assumeyes create --container "${container_name}" --image "${image}" >/dev/null \
+    || fail "Toolbx couldn't create container '$container_name'"
+}
+
+
 function start_container() {
   local container_name
   container_name="$1"