diff --git a/completion/notmuch-completion.bash b/completion/notmuch-completion.bash
index 17be6b8f..72a75a94 100644
--- a/completion/notmuch-completion.bash
+++ b/completion/notmuch-completion.bash
@@ -287,12 +287,16 @@ _notmuch_insert()
 		sed "s|^$path/||" | grep -v "\(^\|/\)\(cur\|new\|tmp\)$" ) )
 	    return
 	    ;;
+	--try-decrypt)
+	    COMPREPLY=( $( compgen -W "true false" -- "${cur}" ) )
+	    return
+	    ;;
     esac
 
     ! $split &&
     case "${cur}" in
 	--*)
-	    local options="--create-folder --folder= --keep --no-hooks ${_notmuch_shared_options}"
+	    local options="--create-folder --folder= --keep --no-hooks --try-decrypt= ${_notmuch_shared_options}"
 	    compopt -o nospace
 	    COMPREPLY=( $(compgen -W "$options" -- ${cur}) )
 	    return
diff --git a/doc/man1/notmuch-insert.rst b/doc/man1/notmuch-insert.rst
index f83a7385..e2bf37d0 100644
--- a/doc/man1/notmuch-insert.rst
+++ b/doc/man1/notmuch-insert.rst
@@ -50,6 +50,20 @@ Supported options for **insert** include
     ``--no-hooks``
         Prevent hooks from being run.
 
+    ``--try-decrypt=(true|false)``
+
+        If true and the message is encrypted, try to decrypt the
+        message while indexing.  If decryption is successful, index
+        the cleartext itself.  Either way, the message is always
+        stored to disk in its original form (ciphertext).  Be aware
+        that the index is likely sufficient to reconstruct the
+        cleartext of the message itself, so please ensure that the
+        notmuch message index is adequately protected. DO NOT USE
+        ``--try-decrypt=true`` without considering the security of
+        your index.
+
+        See also ``index.try_decrypt`` in **notmuch-config(1)**.
+
 EXIT STATUS
 ===========
 
diff --git a/notmuch-insert.c b/notmuch-insert.c
index 32be7419..4d6b0a7f 100644
--- a/notmuch-insert.c
+++ b/notmuch-insert.c
@@ -379,12 +379,13 @@ FAIL:
  */
 static notmuch_status_t
 add_file (notmuch_database_t *notmuch, const char *path, tag_op_list_t *tag_ops,
-	  bool synchronize_flags, bool keep)
+	  bool synchronize_flags, bool keep,
+	  notmuch_indexopts_t *indexopts)
 {
     notmuch_message_t *message;
     notmuch_status_t status;
 
-    status = notmuch_database_index_file (notmuch, path, NULL, &message);
+    status = notmuch_database_index_file (notmuch, path, indexopts, &message);
     if (status == NOTMUCH_STATUS_SUCCESS) {
 	status = tag_op_list_apply (message, tag_ops, 0);
 	if (status) {
@@ -467,6 +468,7 @@ notmuch_insert_command (notmuch_config_t *config, int argc, char *argv[])
 	{ .opt_bool = &create_folder, .name = "create-folder" },
 	{ .opt_bool = &keep, .name = "keep" },
 	{ .opt_bool =  &no_hooks, .name = "no-hooks" },
+	{ .opt_inherit = notmuch_shared_indexing_options },
 	{ .opt_inherit = notmuch_shared_options },
 	{ }
     };
@@ -545,9 +547,15 @@ notmuch_insert_command (notmuch_config_t *config, int argc, char *argv[])
 
     notmuch_exit_if_unmatched_db_uuid (notmuch);
 
+    status = notmuch_process_shared_indexing_options (notmuch, config);
+    if (status != NOTMUCH_STATUS_SUCCESS) {
+	fprintf (stderr, "Error: Failed to process index options. (%s)\n",
+		 notmuch_status_to_string (status));
+	return EXIT_FAILURE;
+    }
 
     /* Index the message. */
-    status = add_file (notmuch, newpath, tag_ops, synchronize_flags, keep);
+    status = add_file (notmuch, newpath, tag_ops, synchronize_flags, keep, indexing_cli_choices.opts);
 
     /* Commit changes. */
     close_status = notmuch_database_destroy (notmuch);
diff --git a/test/T357-index-decryption.sh b/test/T357-index-decryption.sh
index 547a3c7e..1e60df04 100755
--- a/test/T357-index-decryption.sh
+++ b/test/T357-index-decryption.sh
@@ -48,4 +48,60 @@ test_expect_equal \
     "$output" \
     "$expected"
 
+
+test_begin_subtest "message should go away after deletion"
+# cache the message in an env var and remove it:
+fname=$(notmuch search --output=files wumpus)
+contents="$(notmuch show --format=raw wumpus)"
+rm -f "$fname"
+notmuch new
+output=$(notmuch search wumpus)
+expected=''
+test_expect_equal \
+    "$output" \
+    "$expected"
+
+# try reinserting it without decryption, should stay the same:
+test_begin_subtest "message cleartext not present after insert"
+notmuch insert --folder=sent <<<"$contents"
+output=$(notmuch search wumpus)
+test_expect_equal \
+    "$output" \
+    "$expected"
+
+# try reinserting it with decryption, should appear again, but now we
+# have two copies of the message:
+test_begin_subtest "message cleartext is present after reinserting with --try-decrypt"
+notmuch insert --folder=sent --try-decrypt <<<"$contents"
+output=$(notmuch search wumpus)
+expected='thread:0000000000000003   2000-01-01 [1/1(2)] Notmuch Test Suite; test encrypted message for cleartext index 002 (encrypted inbox unread)'
+test_expect_equal \
+    "$output" \
+    "$expected"
+
+# remove all copies
+test_begin_subtest "delete all copies of the message"
+mid="$(notmuch search --output=messages wumpus)"
+rm -f $(notmuch search --output=files wumpus)
+notmuch new
+output=$(notmuch search "id:$mid")
+expected=''
+test_expect_equal \
+    "$output" \
+    "$expected"
+
+# try inserting it with decryption, should appear as a single copy
+# (note: i think thread id skips 4 because of duplicate message-id
+# insertion, above)
+test_begin_subtest "message cleartext is present with insert --try-decrypt"
+notmuch insert --folder=sent --try-decrypt <<<"$contents"
+output=$(notmuch search wumpus)
+expected='thread:0000000000000005   2000-01-01 [1/1] Notmuch Test Suite; test encrypted message for cleartext index 002 (encrypted inbox unread)'
+test_expect_equal \
+    "$output" \
+    "$expected"
+
+
+
+
 test_done