diff --git a/Annex/Content.hs b/Annex/Content.hs
index 8dd1dec0f2..da65143ab4 100644
--- a/Annex/Content.hs
+++ b/Annex/Content.hs
@@ -632,18 +632,20 @@ saveState nocommit = doSideAction $ do
 			Annex.Branch.commit =<< Annex.Branch.commitMessage
 
 {- Downloads content from any of a list of urls, displaying a progress
- - meter. -}
-downloadUrl :: Key -> MeterUpdate -> Maybe IncrementalVerifier -> [Url.URLString] -> FilePath -> Url.UrlOptions -> Annex Bool
-downloadUrl k p iv urls file uo = 
+ - meter.
+ -
+ - Only displays error message if all the urls fail to download.
+ - When listfailedurls is set, lists each url and why it failed.
+ - Otherwise, only displays one error message, from one of the urls
+ - that failed.
+ -}
+downloadUrl :: Bool -> Key -> MeterUpdate -> Maybe IncrementalVerifier -> [Url.URLString] -> FilePath -> Url.UrlOptions -> Annex Bool
+downloadUrl listfailedurls k p iv urls file uo = 
 	-- Poll the file to handle configurations where an external
 	-- download command is used.
-	meteredFile file (Just p) k (go urls Nothing)
+	meteredFile file (Just p) k (go urls [])
   where
-  	-- Display only one error message, if all the urls fail to
-	-- download.
-	go [] (Just err) = warning err >> return False
-	go [] Nothing = return False
-	go (u:us) _ = Url.download' p iv u file uo >>= \case
+	go (u:us) errs = Url.download' p iv u file uo >>= \case
 		Right () -> return True
 		Left err -> do
 			-- If the incremental verifier was fed anything
@@ -655,7 +657,14 @@ downloadUrl k p iv urls file uo =
 					Just n | n > 0 -> unableIncremental iv'
 					_ -> noop
 				Nothing -> noop
-			go us (Just err)
+			go us ((u, err) : errs)
+	go [] [] = return False
+	go [] errs@((_, err):_) = do
+		if listfailedurls
+			then warning $ unlines $ flip map errs $ \(u, err') ->
+				u ++ " " ++ err'
+			else warning err
+		return False
 
 {- Copies a key's content, when present, to a temp file.
  - This is used to speed up some rsyncs. -}
diff --git a/CHANGELOG b/CHANGELOG
index 897b010072..7cb757be5f 100644
--- a/CHANGELOG
+++ b/CHANGELOG
@@ -26,6 +26,10 @@ git-annex (8.20210804) UNRELEASED; urgency=medium
     a file's content, and fail with an informative message.
   * Fix support for readonly git remotes.
     (Reversion in version 8.20210621)
+  * When downloading urls fail, explain which urls failed for which
+    reasons.
+  * web: Avoid displaying a warning when downloading one url failed
+    but another url later succeeded.
 
  -- Joey Hess <id@joeyh.name>  Tue, 03 Aug 2021 12:22:45 -0400
 
diff --git a/Command/AddUrl.hs b/Command/AddUrl.hs
index eb99119ac4..f256aed2d8 100644
--- a/Command/AddUrl.hs
+++ b/Command/AddUrl.hs
@@ -314,7 +314,7 @@ downloadWeb addunlockedmatcher o url urlinfo file =
 	go =<< downloadWith' downloader urlkey webUUID url (AssociatedFile (Just file))
   where
 	urlkey = addSizeUrlKey urlinfo $ Backend.URL.fromUrl url Nothing
-	downloader f p = Url.withUrlOptions $ downloadUrl urlkey p Nothing [url] f
+	downloader f p = Url.withUrlOptions $ downloadUrl False urlkey p Nothing [url] f
 	go Nothing = return Nothing
 	go (Just tmp) = ifM (pure (not (rawOption o)) <&&> liftIO (isHtmlFile (fromRawFilePath tmp)))
 		( tryyoutubedl tmp
diff --git a/Remote/External.hs b/Remote/External.hs
index 102b6caeff..1137cd74f5 100644
--- a/Remote/External.hs
+++ b/Remote/External.hs
@@ -810,7 +810,7 @@ checkUrlM external url =
 retrieveUrl :: Retriever
 retrieveUrl = fileRetriever' $ \f k p iv -> do
 	us <- getWebUrls k
-	unlessM (withUrlOptions $ downloadUrl k p iv us (fromRawFilePath f)) $
+	unlessM (withUrlOptions $ downloadUrl True k p iv us (fromRawFilePath f)) $
 		giveup "failed to download content"
 
 checkKeyUrl :: CheckPresent
diff --git a/Remote/Git.hs b/Remote/Git.hs
index 8d97c59a28..81a6bc5fdf 100644
--- a/Remote/Git.hs
+++ b/Remote/Git.hs
@@ -543,7 +543,7 @@ copyFromRemote'' repo forcersync r st@(State connpool _ _ _ _) key file dest met
 		iv <- startVerifyKeyContentIncrementally vc key
 		gc <- Annex.getGitConfig
 		ok <- Url.withUrlOptionsPromptingCreds $
-			Annex.Content.downloadUrl key meterupdate iv (keyUrls gc repo r key) dest
+			Annex.Content.downloadUrl False key meterupdate iv (keyUrls gc repo r key) dest
 		unless ok $
 			giveup "failed to download content"
 		snd <$> finishVerifyKeyContentIncrementally iv
diff --git a/Remote/S3.hs b/Remote/S3.hs
index 9e0fd01f4a..7a4a8541b2 100644
--- a/Remote/S3.hs
+++ b/Remote/S3.hs
@@ -414,7 +414,7 @@ retrieve hv r rs c info = fileRetriever' $ \f k p iv -> withS3Handle hv $ \case
 			Left failreason -> do
 				warning failreason
 				giveup "cannot download content"
-			Right us -> unlessM (withUrlOptions $ downloadUrl k p iv us (fromRawFilePath f)) $
+			Right us -> unlessM (withUrlOptions $ downloadUrl False k p iv us (fromRawFilePath f)) $
 				giveup "failed to download content"
 
 retrieveHelper :: S3Info -> S3Handle -> (Either S3.Object S3VersionID) -> FilePath -> MeterUpdate -> Maybe IncrementalVerifier -> Annex ()
diff --git a/Remote/Web.hs b/Remote/Web.hs
index 938881e37a..94e9391e33 100644
--- a/Remote/Web.hs
+++ b/Remote/Web.hs
@@ -86,26 +86,30 @@ downloadKey :: Key -> AssociatedFile -> FilePath -> MeterUpdate -> VerifyConfig
 downloadKey key _af dest p vc = go =<< getWebUrls key
   where
 	go [] = giveup "no known url"
-	go urls = getM dl urls >>= \case
+	go urls = dl (partition (not . isyoutube) (map getDownloader urls)) >>= \case
 		Just v -> return v
-		Nothing -> giveup "download failed"
+		Nothing -> giveup $ unwords
+			[ "downloading from all"
+			, show (length urls)
+			, "known url(s) failed"
+			]
 
-	dl u = do
-		let (u', downloader) = getDownloader u
-		case downloader of
-			YoutubeDownloader ->
-				ifM (youtubeDlTo key u' dest p)
-					( return (Just UnVerified)
-					, return Nothing
-					)
-			_ -> do
-				iv <- startVerifyKeyContentIncrementally vc key
-				ifM (Url.withUrlOptions $ downloadUrl key p iv [u'] dest)
-					( finishVerifyKeyContentIncrementally iv >>= \case
-						(True, v) -> return (Just v)
-						(False, _) -> return Nothing
-					, return Nothing
-					)
+	dl ([], ytus) = flip getM (map fst ytus) $ \u ->
+		ifM (youtubeDlTo key u dest p)
+			( return (Just UnVerified)
+			, return Nothing
+			)
+	dl (us, ytus) = do
+		iv <- startVerifyKeyContentIncrementally vc key
+		ifM (Url.withUrlOptions $ downloadUrl True key p iv (map fst us) dest)
+			( finishVerifyKeyContentIncrementally iv >>= \case
+				(True, v) -> return (Just v)
+				(False, _) -> dl ([], ytus)
+			, dl ([], ytus)
+			)
+
+	isyoutube (_, YoutubeDownloader) = True
+	isyoutube _ = False
 
 uploadKey :: Key -> AssociatedFile -> MeterUpdate -> Annex ()
 uploadKey _ _ _ = giveup "upload to web not supported"
diff --git a/doc/todo/get__58___improve_error_reporting_for_failed_attempts.mdwn b/doc/todo/get__58___improve_error_reporting_for_failed_attempts.mdwn
index 0a79c556f3..3b89164781 100644
--- a/doc/todo/get__58___improve_error_reporting_for_failed_attempts.mdwn
+++ b/doc/todo/get__58___improve_error_reporting_for_failed_attempts.mdwn
@@ -41,3 +41,15 @@ refs in DataLad issues:
 
 - from web remote: ["download failed: Not Found"](https://github.com/datalad/datalad/pull/5936)
 - from ["failed to retrieve content from remote"](https://github.com/datalad/datalad/issues/5750)
+
+> I think this is specific to downloading urls, although it can happen
+> for a few remotes (web, external). There's really no reason to display
+> a download failed message if it successfully downloads a later url.
+> (After all, if it had tried the working url first, it would never display
+> anything about the broken url.)
+> 
+> When all urls fail, it makes sense to display each url and why it failed
+> when using the web (or external) remote, so the user can decide what to
+> do about each of the problems.
+> 
+> [[done]] --[[Joey]]