diff --git a/src/Messages/OWSFailedAttachmentDownloadsJob.h b/src/Messages/OWSFailedAttachmentDownloadsJob.h
new file mode 100644
index 000000000..7ad6b20ee
--- /dev/null
+++ b/src/Messages/OWSFailedAttachmentDownloadsJob.h
@@ -0,0 +1,28 @@
+//
+//  Copyright (c) 2017 Open Whisper Systems. All rights reserved.
+//
+
+NS_ASSUME_NONNULL_BEGIN
+
+@class TSStorageManager;
+
+@interface OWSFailedAttachmentDownloadsJob : NSObject
+
+- (instancetype)init NS_UNAVAILABLE;
+- (instancetype)initWithStorageManager:(TSStorageManager *)storageManager NS_DESIGNATED_INITIALIZER;
+
+- (void)run;
+
+/**
+ * Database extensions required for class to work.
+ */
+- (void)asyncRegisterDatabaseExtensions;
+
+/**
+ * Only use the sync version for testing, generally we'll want to register extensions async
+ */
+- (void)blockingRegisterDatabaseExtensions;
+
+@end
+
+NS_ASSUME_NONNULL_END
diff --git a/src/Messages/OWSFailedAttachmentDownloadsJob.m b/src/Messages/OWSFailedAttachmentDownloadsJob.m
new file mode 100644
index 000000000..ccd215513
--- /dev/null
+++ b/src/Messages/OWSFailedAttachmentDownloadsJob.m
@@ -0,0 +1,148 @@
+//
+//  Copyright (c) 2017 Open Whisper Systems. All rights reserved.
+//
+
+#import "OWSFailedAttachmentDownloadsJob.h"
+#import "TSAttachmentPointer.h"
+#import "TSStorageManager.h"
+#import <YapDatabase/YapDatabaseConnection.h>
+#import <YapDatabase/YapDatabaseQuery.h>
+#import <YapDatabase/YapDatabaseSecondaryIndex.h>
+
+NS_ASSUME_NONNULL_BEGIN
+
+static NSString *const OWSFailedAttachmentDownloadsJobAttachmentStateColumn = @"state";
+static NSString *const OWSFailedAttachmentDownloadsJobAttachmentStateIndex = @"index_attachment_downloads_on_state";
+
+@interface OWSFailedAttachmentDownloadsJob ()
+
+@property (nonatomic, readonly) TSStorageManager *storageManager;
+
+@end
+
+#pragma mark -
+
+@implementation OWSFailedAttachmentDownloadsJob
+
+- (instancetype)initWithStorageManager:(TSStorageManager *)storageManager
+{
+    self = [super init];
+    if (!self) {
+        return self;
+    }
+
+    _storageManager = storageManager;
+
+    return self;
+}
+
+- (NSArray<NSString *> *)fetchAttemptingOutAttachmentIds:(YapDatabaseConnection *)dbConnection
+{
+    NSMutableArray<NSString *> *attachmentIds = [NSMutableArray new];
+
+    NSString *formattedString = [NSString stringWithFormat:@"WHERE %@ != %d",
+                                          OWSFailedAttachmentDownloadsJobAttachmentStateColumn,
+                                          (int)TSAttachmentPointerStateFailed];
+    YapDatabaseQuery *query = [YapDatabaseQuery queryWithFormat:formattedString];
+    [dbConnection readWithBlock:^(YapDatabaseReadTransaction *_Nonnull transaction) {
+        [[transaction ext:OWSFailedAttachmentDownloadsJobAttachmentStateIndex]
+            enumerateKeysMatchingQuery:query
+                            usingBlock:^void(NSString *collection, NSString *key, BOOL *stop) {
+                                [attachmentIds addObject:key];
+                            }];
+    }];
+
+    return [attachmentIds copy];
+}
+
+- (void)enumerateAttemptingOutAttachmentsWithBlock:(void (^_Nonnull)(TSAttachmentPointer *attachment))block
+{
+    YapDatabaseConnection *dbConnection = [self.storageManager newDatabaseConnection];
+
+    // Since we can't directly mutate the enumerated attachments, we store only their ids in hopes
+    // of saving a little memory and then enumerate the (larger) TSAttachment objects one at a time.
+    for (NSString *attachmentId in [self fetchAttemptingOutAttachmentIds:dbConnection]) {
+        TSAttachmentPointer *_Nullable attachment = [TSAttachmentPointer fetchObjectWithUniqueID:attachmentId];
+        if ([attachment isKindOfClass:[TSAttachmentPointer class]]) {
+            block(attachment);
+        } else {
+            DDLogError(@"%@ unexpected object: %@", self.tag, attachment);
+        }
+    }
+}
+
+- (void)run
+{
+    __block uint count = 0;
+    [self enumerateAttemptingOutAttachmentsWithBlock:^(TSAttachmentPointer *attachment) {
+        // sanity check
+        if (attachment.state != TSAttachmentPointerStateFailed) {
+            DDLogDebug(@"%@ marking attachment as failed", self.tag);
+            attachment.state = TSAttachmentPointerStateFailed;
+            [attachment save];
+            count++;
+        }
+    }];
+
+    DDLogDebug(@"%@ Marked %u attachments as unsent", self.tag, count);
+}
+
+#pragma mark - YapDatabaseExtension
+
+- (YapDatabaseSecondaryIndex *)indexDatabaseExtension
+{
+    YapDatabaseSecondaryIndexSetup *setup = [YapDatabaseSecondaryIndexSetup new];
+    [setup addColumn:OWSFailedAttachmentDownloadsJobAttachmentStateColumn
+            withType:YapDatabaseSecondaryIndexTypeInteger];
+
+    YapDatabaseSecondaryIndexHandler *handler =
+        [YapDatabaseSecondaryIndexHandler withObjectBlock:^(YapDatabaseReadTransaction *transaction,
+            NSMutableDictionary *dict,
+            NSString *collection,
+            NSString *key,
+            id object) {
+            if (![object isKindOfClass:[TSAttachmentPointer class]]) {
+                return;
+            }
+            TSAttachmentPointer *attachment = (TSAttachmentPointer *)object;
+            dict[OWSFailedAttachmentDownloadsJobAttachmentStateColumn] = @(attachment.state);
+        }];
+
+    return [[YapDatabaseSecondaryIndex alloc] initWithSetup:setup handler:handler];
+}
+
+// Useful for tests, don't use in app startup path because it's slow.
+- (void)blockingRegisterDatabaseExtensions
+{
+    [self.storageManager.database registerExtension:[self indexDatabaseExtension]
+                                           withName:OWSFailedAttachmentDownloadsJobAttachmentStateIndex];
+}
+
+- (void)asyncRegisterDatabaseExtensions
+{
+    [self.storageManager.database asyncRegisterExtension:[self indexDatabaseExtension]
+                                                withName:OWSFailedAttachmentDownloadsJobAttachmentStateIndex
+                                         completionBlock:^(BOOL ready) {
+                                             if (ready) {
+                                                 DDLogDebug(@"%@ completed registering extension async.", self.tag);
+                                             } else {
+                                                 DDLogError(@"%@ failed registering extension async.", self.tag);
+                                             }
+                                         }];
+}
+
+#pragma mark - Logging
+
++ (NSString *)tag
+{
+    return [NSString stringWithFormat:@"[%@]", self.class];
+}
+
+- (NSString *)tag
+{
+    return self.class.tag;
+}
+
+@end
+
+NS_ASSUME_NONNULL_END
diff --git a/src/Storage/TSStorageManager.m b/src/Storage/TSStorageManager.m
index c3d9a613d..eaca489b8 100644
--- a/src/Storage/TSStorageManager.m
+++ b/src/Storage/TSStorageManager.m
@@ -6,6 +6,7 @@
 #import "NSData+Base64.h"
 #import "OWSAnalytics.h"
 #import "OWSDisappearingMessagesFinder.h"
+#import "OWSFailedAttachmentDownloadsJob.h"
 #import "OWSFailedMessagesJob.h"
 #import "OWSIncomingMessageFinder.h"
 #import "OWSReadReceipt.h"
@@ -205,6 +206,9 @@ static NSString *keychainDBPassAccount    = @"TSDatabasePass";
     [finder asyncRegisterDatabaseExtensions];
     OWSFailedMessagesJob *failedMessagesJob = [[OWSFailedMessagesJob alloc] initWithStorageManager:self];
     [failedMessagesJob asyncRegisterDatabaseExtensions];
+    OWSFailedAttachmentDownloadsJob *failedAttachmentDownloadsMessagesJob =
+        [[OWSFailedAttachmentDownloadsJob alloc] initWithStorageManager:self];
+    [failedAttachmentDownloadsMessagesJob asyncRegisterDatabaseExtensions];
 }
 
 - (void)protectSignalFiles {