diff --git a/changelog.md b/changelog.md
index 08e073a57..cd02ffb0e 100644
--- a/changelog.md
+++ b/changelog.md
@@ -11,6 +11,9 @@
   - steam protocol has changed profoundly
   - keybase has been removed because we don't have a maintainer for it. See
     [issue #9](https://github.com/matterbridge-org/matterbridge/issues/9)
+- During attachment filename sanitation, extensions are also sanitized
+- Attachment filenames are truncated to 50 characters, and discarded entirely
+  when extension (anything after the first `.`) is longer than that
 - matrix: Change to mautrix.go for the matrix backend. See ([pr #79](https://github.com/matterbridge-org/matterbridge/pull/79)/[issue #60](https://github.com/matterbridge-org/matterbridge/issues/60)
 - xmpp: Initial replies/edits support has been removed, because it was incorrect ([#12](https://github.com/matterbridge-org/matterbridge/pull/12))
 - xmpp: `NoTls` setting has been deprecated; to disable `StartTls` and start a plaintext connection, use `NoStartTls`
diff --git a/gateway/handlers.go b/gateway/handlers.go
index b934f5343..aa7abb79b 100644
--- a/gateway/handlers.go
+++ b/gateway/handlers.go
@@ -4,7 +4,6 @@ import (
 	"crypto/sha1" //nolint:gosec
 	"fmt"
 	"os"
-	"path/filepath"
 	"regexp"
 	"strings"
 
@@ -13,6 +12,8 @@ import (
 	"github.com/matterbridge-org/matterbridge/gateway/bridgemap"
 )
 
+var REGEX_EXCLUDE_FILENAME_CHARS = regexp.MustCompile("[^a-zA-Z0-9\\.]+")
+
 // handleEventFailure handles failures and reconnects bridges.
 func (r *Router) handleEventFailure(msg *config.Message) {
 	if msg.Event != config.EventFailure {
@@ -65,8 +66,6 @@ func (r *Router) handleEventRejoinChannels(msg *config.Message) {
 // handleFiles uploads or places all files on the given msg to the MediaServer and
 // adds the new URL of the file on the MediaServer onto the given msg.
 func (gw *Gateway) handleFiles(msg *config.Message) {
-	reg := regexp.MustCompile("[^a-zA-Z0-9]+")
-
 	// If we don't have a attachfield or we don't have a mediaserver configured return
 	if msg.Extra == nil || gw.BridgeValues().General.MediaDownloadPath == "" {
 		return
@@ -77,13 +76,65 @@ func (gw *Gateway) handleFiles(msg *config.Message) {
 		return
 	}
 
-	for i, f := range msg.Extra["file"] {
+	// Here we will store the information about attachments that
+	// we want to keep after sanitation.
+	sanitizedFiles := []interface{}{}
+
+	for _, f := range msg.Extra["file"] {
 		fi := f.(config.FileInfo)
-		ext := filepath.Ext(fi.Name)
-		fi.Name = fi.Name[0 : len(fi.Name)-len(ext)]
-		fi.Name = reg.ReplaceAllString(fi.Name, "_")
-		fi.Name += ext
 
+		// Sanitation: every sequence of non-alphanumreic chars is replaced by a single `_`
+		// in the filename, including the extension. We allow `.` to keep the extension.
+		fi.Name = REGEX_EXCLUDE_FILENAME_CHARS.ReplaceAllString(fi.Name, "_")
+
+		// Sanitation: limit filename to 50 characters. It looks like 255 bytes is a common
+		// accepted value: https://en.wikipedia.org/wiki/Comparison_of_file_systems#Limits
+		// However, we do not wish to produce too long filenames which will be badly displayed
+		// in remote clients.
+		charLimit := 50
+
+		// First, filter out any path that's longer than 254 bytes and consider it malicious.
+		if len(fi.Name) > 254 {
+			gw.logger.Infof("Filename >=255B received from %s on channel %s (%s), dropping the attachment %s...", msg.Username, msg.Channel, msg.Gateway, fi.Name[0:49])
+			continue
+		}
+
+		if len(fi.Name) > charLimit {
+			gw.logger.Warn("filename too long")
+			// We want to limit the size of the first part (before the extension), not of
+			// the extension. Also, we want to make sure we don't end up removing a part
+			// of the extension, so we don't use `filepath.Ext` which could incite us
+			// to sanitize `TOOLONG.tar.xz` into `OK.xz`, omitting crucial information.
+			removeN := len(fi.Name) - charLimit
+			parts := strings.Split(fi.Name, ".")
+			if len(parts[0]) > removeN {
+				// We can successfully remove N characters from the first part of the path
+				parts[0] = parts[0][0 : len(parts[0])-removeN]
+				fi.Name = strings.Join(parts, ".")
+			} else {
+				// Maybe the filename is malicious, maybe it is not.
+				// If the part after the last dot (extension) is itself too long,
+				// we just give up. We check for 48 chars because we want one char
+				// before the extension.
+				if len(parts[len(parts)-1]) > (charLimit - 2) {
+					gw.logger.Infof("Too long filename received from %s on channel %s (%s), dropping the attachment %s...", msg.Username, msg.Channel, msg.Gateway, fi.Name[0:charLimit])
+					continue
+				} else {
+					// We still have a chance. Remove chars from the start of path until
+					// it's short enough.
+					fi.Name = strings.Join(parts, ".")
+					fi.Name = fi.Name[:charLimit]
+				}
+			}
+
+			gw.logger.Debugf("Sanitized too long filename to %s", fi.Name)
+		}
+
+	}
+
+	msg.Extra["file"] = sanitizedFiles
+	for i, f := range msg.Extra["file"] {
+		fi := f.(config.FileInfo)
 		sha1sum := fmt.Sprintf("%x", sha1.Sum(*fi.Data))[:8] //nolint:gosec
 
 		// Use MediaServerPath. Place the file on the current filesystem.
@@ -99,10 +150,9 @@ func (gw *Gateway) handleFiles(msg *config.Message) {
 		gw.logger.Debugf("mediaserver download URL = %s", durl)
 
 		// We uploaded/placed the file successfully. Add the SHA and URL.
-		extra := msg.Extra["file"][i].(config.FileInfo)
-		extra.URL = durl
-		extra.SHA = sha1sum
-		msg.Extra["file"][i] = extra
+		fi.URL = durl
+		fi.SHA = sha1sum
+		msg.Extra["file"][i] = fi
 	}
 }