diff --git a/internal/slackclient/slack_messages.go b/internal/slackclient/slack_messages.go
index 6fded60..3b27ae6 100644
--- a/internal/slackclient/slack_messages.go
+++ b/internal/slackclient/slack_messages.go
@@ -93,3 +93,22 @@ func PostSlackMessage(client *SlackClient, channel string, opts SlackPostMessage
 
 	return ts, error
 }
+
+// PostSlackMessage allows posting messages to specific channels
+func SendDirectMessage(client *SlackClient, userId string, message string) (timestamp string, error error) {
+	reactedMessageBlock := slack.NewTextBlockObject(slack.MarkdownType, message, false, false)
+
+	blocks := []slack.Block{
+		slack.NewSectionBlock(reactedMessageBlock, nil, nil),
+	}
+
+	_, ts, error := client.PostMessage(
+		userId,
+		slack.MsgOptionBlocks(blocks...),
+		slack.MsgOptionText(message, true),
+		slack.MsgOptionAsUser(false),
+		slack.MsgOptionParse(true),
+	)
+
+	return ts, error
+}
diff --git a/reactionbot/events.go b/reactionbot/events.go
index a2ccf67..4af2977 100644
--- a/reactionbot/events.go
+++ b/reactionbot/events.go
@@ -1,14 +1,119 @@
 package reactionbot
 
-import "github.com/jordanleven/reaction-bot/internal/slackclient"
+import (
+	"fmt"
+	"path/filepath"
+	"strings"
 
-func (r reactionBot) messageShouldBePosted(event slackclient.ReactionEvent) bool {
-	return r.reactionIsRegistered(event.ReactionEmoji) && event.ReactionCount == 1
+	"github.com/fatih/color"
+	"github.com/jordanleven/reaction-bot/internal/slackclient"
+)
+
+type eventReactionStatus int
+
+// Enums for handling eligible and ineligible posts
+const (
+	eventReactionEligible eventReactionStatus = iota
+	eventReactionIneligibleUserReactedToDoesNotExist
+	eventReactionIneligibleMessageContainsDisallowedAttachmentType
+	eventReactionIneligibleUnknownReason
+)
+
+const (
+	eventReactionIneligibleMessageIntro = "Hey {user}, Reaction Bot here :robot_face:! It looks like you recently added a \":{reactionType}:\" reaction to a message (\"{message}\") that I'm unable to work with."
+	eventReactionIneligibleMessageOutro = "Sorry about that, but I hope we can still be friends! :heart:"
+)
+
+var eventReactionStatusErrorMessages = map[eventReactionStatus]string{
+	eventReactionIneligibleUserReactedToDoesNotExist:               "Posting a reaction on messages that originate from Slack Bots and Apps is unsupported.",
+	eventReactionIneligibleMessageContainsDisallowedAttachmentType: "Posting a reaction on messages that contain `{attachmentExtension}` attachments is currently not supported by Slack.",
+	eventReactionIneligibleUnknownReason:                           "",
+}
+
+var eventReactionDisallowedAttachmentTypes = []string{
+	"webm",
+}
+
+func eventReactionMessageContainsDisallowedAttachmentType(event slackclient.ReactionEvent) bool {
+	// Early exist if no attachment is contained
+	if event.MessageAttachment == nil {
+		return false
+	}
+
+	attachmentExtension := filepath.Ext(event.MessageAttachment.Name)
+
+	for _, v := range eventReactionDisallowedAttachmentTypes {
+		vF := fmt.Sprintf(".%s", v)
+		if attachmentExtension == vF {
+			return true
+		}
+	}
+
+	return false
+}
+
+func (r reactionBot) eventReactionIsEligibleForPost(event slackclient.ReactionEvent) (bool, eventReactionStatus) {
+	// User IDs will only exist for messages posted by real users
+	userIdDoesNotExist := event.UserIDReactedTo == ""
+	messageContainsDisallowedAttachment := eventReactionMessageContainsDisallowedAttachmentType(event)
+
+	messageIsEligibleForPost := !userIdDoesNotExist && !messageContainsDisallowedAttachment
+
+	switch {
+	case messageIsEligibleForPost:
+		return messageIsEligibleForPost, eventReactionEligible
+	case userIdDoesNotExist:
+		return messageIsEligibleForPost, eventReactionIneligibleUserReactedToDoesNotExist
+	case messageContainsDisallowedAttachment:
+		return messageIsEligibleForPost, eventReactionIneligibleMessageContainsDisallowedAttachmentType
+	default:
+		return messageIsEligibleForPost, eventReactionIneligibleUnknownReason
+	}
+}
+
+func (r reactionBot) eventReactionIsRegistered(event slackclient.ReactionEvent) bool {
+	return r.reactionIsRegistered(event.ReactionEmoji)
+}
+
+func eventReactionIsUnique(event slackclient.ReactionEvent) bool {
+	return event.ReactionCount == 1
+}
+
+func (r reactionBot) sentEventIneligibleMessageToUser(status eventReactionStatus, event slackclient.ReactionEvent) {
+	allUsers := r.Users
+	reactedByUser := getUserByUserID(*allUsers, event.UserIDReactedBy)
+	var attachmentExtension string
+
+	if event.MessageAttachment != nil {
+		attachmentExtension = filepath.Ext(event.MessageAttachment.Name)
+	}
+
+	statusSpecificErrorMessage := eventReactionStatusErrorMessages[status]
+	errorMessage := fmt.Sprintf("%s %s \n \n %s", eventReactionIneligibleMessageIntro, statusSpecificErrorMessage, eventReactionIneligibleMessageOutro)
+
+	errorMessageReplacements := strings.NewReplacer(
+		"{user}", reactedByUser.DisplayName,
+		"{message}", event.Message,
+		"{attachmentExtension}", attachmentExtension,
+		"{reactionType}", event.ReactionEmoji,
+	)
+	errorMessageF := errorMessageReplacements.Replace(errorMessage)
+
+	slackclient.SendDirectMessage(r.SlackClient, event.UserIDReactedBy, errorMessageF)
+	color.Yellow("Sent error message to %s. Message unable to reacted to (code %d). Original message was \"%s\". (dated %s).\n", reactedByUser.DisplayName, status, event.Message, event.ReactionTimestamp)
 }
 
 func (r reactionBot) handleReaction(event slackclient.ReactionEvent) {
-	if r.messageShouldBePosted(event) {
+	// Early exist if the reaction isn't something we need to deal with
+	if !r.eventReactionIsRegistered(event) || !eventReactionIsUnique(event) {
+		return
+	}
+
+	isEligibleForPost, status := r.eventReactionIsEligibleForPost(event)
+	if isEligibleForPost {
 		r.maybePostReactedMessageToChannel(event)
+	} else {
+		r.sentEventIneligibleMessageToUser(status, event)
 	}
 }