diff --git a/cmd/config.go b/cmd/config.go
index 7216e6b25..b293ff787 100644
--- a/cmd/config.go
+++ b/cmd/config.go
@@ -26,6 +26,7 @@ type configOptions struct {
 // Path to the config.yml file to operate on.
 // Used to for compatibility with `circleci config validate --path`
 var configPath string
+var ignoreDeprecatedImages bool // should we ignore deprecated images warning
 
 var configAnnotations = map[string]string{
 	"<path>": "The path to your config (use \"-\" for STDIN)",
@@ -71,6 +72,7 @@ func newConfigCommand(config *settings.Config) *cobra.Command {
 	}
 	validateCommand.Annotations["<path>"] = configAnnotations["<path>"]
 	validateCommand.PersistentFlags().StringVarP(&configPath, "config", "c", ".circleci/config.yml", "path to config file")
+	validateCommand.PersistentFlags().BoolVar(&ignoreDeprecatedImages, "ignore-deprecated-images", false, "ignores the deprecated images error")
 	if err := validateCommand.PersistentFlags().MarkHidden("config"); err != nil {
 		panic(err)
 	}
@@ -132,11 +134,21 @@ func validateConfig(opts configOptions, flags *pflag.FlagSet) error {
 
 	orgSlug, _ := flags.GetString("org-slug")
 
-	_, err := api.ConfigQuery(opts.cl, path, orgSlug, nil, pipeline.LocalPipelineValues())
+	response, err := api.ConfigQuery(opts.cl, path, orgSlug, nil, pipeline.LocalPipelineValues())
 	if err != nil {
 		return err
 	}
 
+	// check if a deprecated Linux VM image is being used
+	// link here to blog post when available
+	// returns an error if a deprecated image is used
+	if !ignoreDeprecatedImages {
+		err := deprecatedImageCheck(response)
+		if err != nil {
+			return err
+		}
+	}
+
 	if path == "-" {
 		fmt.Printf("Config input is valid.\n")
 	} else {
diff --git a/cmd/deprecated-images.go b/cmd/deprecated-images.go
new file mode 100644
index 000000000..607edfc88
--- /dev/null
+++ b/cmd/deprecated-images.go
@@ -0,0 +1,75 @@
+package cmd
+
+import (
+	"github.com/CircleCI-Public/circleci-cli/api"
+
+	"github.com/pkg/errors"
+	"gopkg.in/yaml.v3"
+)
+
+// CircleCI Linux VM images that will be permanently removed on May 31st.
+var deprecatedImages = []string{
+	"circleci/classic:201710-01",
+	"circleci/classic:201703-01",
+	"circleci/classic:201707-01",
+	"circleci/classic:201708-01",
+	"circleci/classic:201709-01",
+	"circleci/classic:201710-02",
+	"circleci/classic:201711-01",
+	"circleci/classic",
+	"circleci/classic:latest",
+	"circleci/classic:edge",
+	"circleci/classic:201808-01",
+	"ubuntu-1604:201903-01",
+	"ubuntu-1604:202004-01",
+	"ubuntu-1604:202007-01",
+	"ubuntu-1604:202010-01",
+	"ubuntu-1604:202101-01",
+	"ubuntu-1604:202104-01",
+}
+
+// Simplified Config -> job Structure for an image
+
+type job struct {
+	Machine interface{} `yaml:"machine"`
+}
+
+// Simplified Config Structure for an image
+type processedConfig struct {
+	Jobs map[string]job `yaml:"jobs"`
+}
+
+// Processes the config down to v2.0, then checks image used against the block list
+func deprecatedImageCheck(response *api.ConfigResponse) error {
+
+	aConfig := processedConfig{}
+	err := yaml.Unmarshal([]byte(response.OutputYaml), &aConfig)
+	if err != nil {
+		return err
+	}
+
+	// check each job
+	for key := range aConfig.Jobs {
+
+		switch aConfig.Jobs[key].Machine.(type) {
+		case bool, nil:
+			// using machine true
+			continue
+		}
+
+		image := aConfig.Jobs[key].Machine.(map[string]interface{})["image"]
+
+		// using the `docker`/`xcode` executors
+		if image == nil {
+			continue
+		}
+
+		for _, v := range deprecatedImages {
+			if image.(string) == v {
+				return errors.New("The config is using a deprecated Linux VM image (" + v + "). Please see https://circleci.com/blog/ubuntu-14-16-image-deprecation/. This error can be ignored by using the '--ignore-deprecated-images' flag.")
+			}
+		}
+	}
+
+	return nil
+}