diff --git a/src/GitTools.jl b/src/GitTools.jl
index a63dcde15a..d1d6551ebc 100644
--- a/src/GitTools.jl
+++ b/src/GitTools.jl
@@ -109,7 +109,12 @@ function clone(io::IO, url, source_path; header=nothing, credentials=nothing, kw
     end
     try
         if use_cli_git()
-            run(pipeline(`git clone --quiet $url $source_path`; stdout=devnull))
+            cmd = `git clone --quiet $url $source_path`
+            try
+                run(pipeline(cmd; stdout=devnull))
+            catch err
+                Pkg.Types.pkgerror("The command $(cmd) failed, error: $err")
+            end
             return LibGit2.GitRepo(source_path)
         else
             mkpath(source_path)
@@ -161,7 +166,12 @@ function fetch(io::IO, repo::LibGit2.GitRepo, remoteurl=nothing; header=nothing,
         if use_cli_git()
             let remoteurl=remoteurl
                 cd(LibGit2.path(repo)) do
-                    run(pipeline(`git fetch -q $remoteurl $(only(refspecs))`; stdout=devnull))
+                    cmd = `git fetch -q $remoteurl $(only(refspecs))`
+                    try
+                        run(pipeline(cmd; stdout=devnull))
+                    catch err
+                        Pkg.Types.pkgerror("The command $(cmd) failed, error: $err")
+                    end
                 end
             end
         else
diff --git a/test/new.jl b/test/new.jl
index dd5e5c731a..0062a8e98b 100644
--- a/test/new.jl
+++ b/test/new.jl
@@ -2687,22 +2687,34 @@ end
 # # Other
 #
 # Note: these tests should be run on clean depots
-@testset "downloads" begin
-    for v in (nothing, "true")
-        withenv("JULIA_PKG_USE_CLI_GIT" => v) do
-            # libgit2 downloads
-            isolate() do
-                Pkg.add("Example"; use_git_for_all_downloads=true)
-                @test haskey(Pkg.dependencies(), exuuid)
-                @eval import $(Symbol(TEST_PKG.name))
-                @test_throws SystemError open(pathof(eval(Symbol(TEST_PKG.name))), "w") do io end  # check read-only
-                Pkg.rm(TEST_PKG.name)
-            end
+for v in (nothing, "true")
+    withenv("JULIA_PKG_USE_CLI_GIT" => v, "GIT_TERMINAL_PROMPT" => 0) do
+        @testset "downloads with JULIA_PKG_USE_CLI_GIT = $v" begin
             isolate() do
                 @testset "libgit2 downloads" begin
-                    Pkg.add(TEST_PKG.name; use_git_for_all_downloads=true)
-                    @test haskey(Pkg.dependencies(), TEST_PKG.uuid)
-                    Pkg.rm(TEST_PKG.name)
+                    @testset "via name" begin
+                        Pkg.add(TEST_PKG.name; use_git_for_all_downloads=true)
+                        @test haskey(Pkg.dependencies(), TEST_PKG.uuid)
+                        @eval import $(Symbol(TEST_PKG.name))
+                        @test_throws SystemError open(pathof(eval(Symbol(TEST_PKG.name))), "w") do io end  # check read-only
+                        Pkg.rm(TEST_PKG.name)
+                    end
+                    if (Base.get_bool_env("JULIA_PKG_USE_CLI_GIT", false) && Sys.iswindows()) == false
+                        # TODO: fix. on GH windows runners cli git will prompt for credentials here
+                        @testset "via url" begin
+                            Pkg.add(url="https://github.com/JuliaLang/Example.jl", use_git_for_all_downloads=true)
+                            @test haskey(Pkg.dependencies(), TEST_PKG.uuid)
+                            Pkg.rm(TEST_PKG.name)
+                        end
+                    end
+                end
+                if !Sys.iswindows()
+                    # TODO: fix. on GH windows runners cli git will prompt for credentials here
+                    @testset "libgit2 failures" begin
+                        doesnotexist = "https://github.com/DoesNotExist/DoesNotExist.jl"
+                        @test_throws Pkg.Types.PkgError Pkg.add(url=doesnotexist, use_git_for_all_downloads=true)
+                        @test_throws Pkg.Types.PkgError Pkg.Registry.add(Pkg.RegistrySpec(url=doesnotexist))
+                    end
                 end
                 @testset "tarball downloads" begin
                     Pkg.add("JSON"; use_only_tarballs_for_downloads=true)