diff --git a/handlers.go b/handlers.go
index 0da8ad5..e675ece 100644
--- a/handlers.go
+++ b/handlers.go
@@ -22,6 +22,20 @@ const (
 	// formParseMaxMemory value is based on the default value that is used in
 	// Request.ParseMultipartForm.
 	formParseMaxMemory = 32 << 20 // 32 MB
+
+	// highOnlineEntropy is the desired entropy of an "unguessable" paste URL
+	// (in bits). It should be chosen such that it should be hard for an
+	// attacker to find *any* key that should not be found.
+	// It is desired that the probability to guess a good key is small.
+	//
+	//                         [ amount of pastes ]
+	//     Pr[ good key ] = ---------------------------
+	//                      [ amount of possible keys ]
+	//
+	// So with a conservative [ amount of pastes ] = 2^32 (= 4 billion), and
+	// an [ amount of possible keys ] = 2^80 then the probability of a correct
+	// guess is 2^-48.
+	highOnlineEntropy = 80
 )
 
 type viewPaste uint
@@ -369,7 +383,11 @@ func shortenURL(tx *bolt.Tx, userURL *url.URL) (*db.Paste, error) {
 // Add a paste (of any kind) to the database with arbitrary content.
 func shorten(tx *bolt.Tx, ty db.PasteType, content []byte) (*db.Paste, error) {
 	// Generate the paste key
-	pasteKey, err := db.GeneratePasteKey(tx)
+	var keyEntropy int
+	if ty == db.PasteTypeFileUpload || ty == db.PasteTypePaste {
+		keyEntropy = highOnlineEntropy
+	}
+	pasteKey, err := db.GeneratePasteKey(tx, keyEntropy)
 	if err != nil {
 		return nil, errors.Wrap(err, "generating paste key")
 	}
diff --git a/internal/db/paste.go b/internal/db/paste.go
index 6f12fba..4fbad07 100644
--- a/internal/db/paste.go
+++ b/internal/db/paste.go
@@ -164,10 +164,13 @@ func (p *Paste) RedirectURL() *url.URL {
 	return urlParse
 }
 
-// GeneratePasteKey generates a key until it is not in the database, the
-// running time of this function is in O(log N), where N is the amount of
+// GeneratePasteKey generates a new paste key. It will ensure that the newly
+// generated paste key does not already exist in the database.
+// The running time of this function is in O(log N), where N is the amount of
 // keys stored in the url-shorten database.
-func GeneratePasteKey(tx *bolt.Tx) (string, error) {
+// In tx, a Bolt transaction is given. Use minimumEntropy to set the mimimum
+// guessing entropy of the generated key.
+func GeneratePasteKey(tx *bolt.Tx, minimumEntropy int) (string, error) {
 	pastesBucket := tx.Bucket([]byte(BucketPastes))
 	if pastesBucket == nil {
 		return "", errors.Errorf("bucket %v does not exist", BucketPastes)
@@ -177,7 +180,7 @@ func GeneratePasteKey(tx *bolt.Tx) (string, error) {
 	var key string
 	for {
 		var err error
-		key, err = generatePasteKeyInner(epoch)
+		key, err = generatePasteKeyInner(epoch, minimumEntropy)
 		if err != nil {
 			return "", errors.Wrap(err, "url-key generation failed")
 		}
@@ -203,8 +206,23 @@ func GeneratePasteKey(tx *bolt.Tx) (string, error) {
 	return key, nil
 }
 
-func generatePasteKeyInner(epoch int) (string, error) {
-	urlKey := make([]byte, 4+epoch)
+// generatePasteKeyInner generates a new paste key, but leaves the
+// uniqueness and is-reserved checks to the caller. That is, it only
+// generates a random key in the correct (syntactical) format.
+// Both epoch and entropy can be used to set the key length. Epoch is used
+// to prevent collisions in retrying to generate new keys. Entropy (in bits)
+// is used to ensure that a new key has at least some amount of guessing
+// entropy.
+func generatePasteKeyInner(epoch, entropy int) (string, error) {
+	minKeyLen := 4
+	entropyEpoch := entropy
+	entropyEpoch -= minKeyLen * 6         // First 4 characters provide 24 bits.
+	entropyEpoch++                        // One bit less because of '0' bit.
+	entropyEpoch = (entropyEpoch-1)/5 + 1 // 5 bits for every added epoch.
+	if epoch < entropyEpoch {
+		epoch = entropyEpoch
+	}
+	urlKey := make([]byte, minKeyLen+epoch)
 	_, err := rand.Read(urlKey)
 	if err != nil {
 		return "", err