diff --git a/connect.c b/connect.c
index c6f76e30829ff2..66247868e84a82 100644
--- a/connect.c
+++ b/connect.c
@@ -1512,7 +1512,14 @@ struct child_process *git_connect(int fd[2], const char *url,
 					     version);
 			}
 		}
-		strvec_push(&conn->args, cmd.buf);
+		if (!conn->use_shell || conn->args.nr > 0 ||
+		    does_cmd_require_shell(prog))
+			 strvec_push(&conn->args, cmd.buf);
+		else {
+			/* avoid running through shell; it's unnecessary */
+			strvec_pushl(&conn->args, prog, path, NULL);
+			conn->use_shell = 0;
+		}
 
 		if (start_command(conn))
 			die(_("unable to fork"));
diff --git a/run-command.c b/run-command.c
index e3e02475ccec50..75eb19936bd646 100644
--- a/run-command.c
+++ b/run-command.c
@@ -291,7 +291,7 @@ static const char **prepare_shell_cmd(struct strvec *out, const char **argv)
 	if (!argv[0])
 		BUG("shell command is empty");
 
-	if (strcspn(argv[0], "|&;<>()$`\\\"' \t\n*?[#~=%") != strlen(argv[0])) {
+	if (does_cmd_require_shell(argv[0])) {
 		strvec_push_nodup(out, git_shell_path());
 		strvec_push(out, "-c");
 
diff --git a/run-command.h b/run-command.h
index 0df25e445f001c..29966fc8f18de0 100644
--- a/run-command.h
+++ b/run-command.h
@@ -200,6 +200,15 @@ int exists_in_PATH(const char *command);
  */
 char *git_shell_path(void);
 
+/**
+ * Determines whether the command needs to run through a shell (for example,
+ * `git-upload-pack` does not need a shell, while `less -R` does).
+ */
+static inline int does_cmd_require_shell(const char *cmd)
+{
+	return strcspn(cmd, "|&;<>()$`\\\"' \t\n*?[#~=%") != strlen(cmd);
+}
+
 /**
  * Start a sub-process. Takes a pointer to a `struct child_process`
  * that specifies the details and returns pipe FDs (if requested).
diff --git a/t/lib-bundle-uri-protocol.sh b/t/lib-bundle-uri-protocol.sh
index de09b6b02e2485..d92eb345e80b92 100644
--- a/t/lib-bundle-uri-protocol.sh
+++ b/t/lib-bundle-uri-protocol.sh
@@ -9,7 +9,7 @@ BUNDLE_URI_TEST_BUNDLE_URI=
 case "$BUNDLE_URI_PROTOCOL" in
 file)
 	BUNDLE_URI_PARENT=file_parent
-	BUNDLE_URI_REPO_URI="file://$PWD/file_parent"
+	BUNDLE_URI_REPO_URI="file://$(pwd)/file_parent"
 	BUNDLE_URI_BUNDLE_URI="$BUNDLE_URI_REPO_URI/fake.bdl"
 	test_set_prereq BUNDLE_URI_FILE
 	;;
diff --git a/t/t1900-repo.sh b/t/t1900-repo.sh
index 51d55f11a5ed66..0e132ffb3e1b0e 100755
--- a/t/t1900-repo.sh
+++ b/t/t1900-repo.sh
@@ -70,7 +70,7 @@ test_expect_success 'setup remote' '
 '
 
 test_repo_info 'shallow repository = true is retrieved correctly' \
-	'git clone --depth 1 "file://$PWD/remote"' 'shallow' 'layout.shallow' 'true'
+	'git clone --depth 1 "file://$(pwd)/remote"' 'shallow' 'layout.shallow' 'true'
 
 test_repo_info 'object.format = sha1 is retrieved correctly' \
 	'git init --object-format=sha1' 'sha1' 'object.format' 'sha1'
diff --git a/t/t3421-rebase-topology-linear.sh b/t/t3421-rebase-topology-linear.sh
index f5b7807abd089d..4c2ed7ef628d7e 100755
--- a/t/t3421-rebase-topology-linear.sh
+++ b/t/t3421-rebase-topology-linear.sh
@@ -37,7 +37,7 @@ test_expect_success 'setup branches and remote tracking' '
 	do
 		git branch branch-$tag $tag || return 1
 	done &&
-	git remote add origin "file://$PWD" &&
+	git remote add origin "file://$(pwd)" &&
 	git fetch origin
 '
 
diff --git a/t/t5150-request-pull.sh b/t/t5150-request-pull.sh
index 270ce6ea48796a..f986d6c1e0f289 100755
--- a/t/t5150-request-pull.sh
+++ b/t/t5150-request-pull.sh
@@ -14,7 +14,7 @@ test_expect_success 'setup' '
 	git clone upstream.git upstream-private &&
 	git clone downstream.git local &&
 
-	trash_url="file://$TRASH_DIRECTORY" &&
+	trash_url="$TRASH_DIRECTORY_URL" &&
 	downstream_url="$trash_url/downstream.git/" &&
 	upstream_url="$trash_url/upstream.git/" &&
 
diff --git a/t/t5318-commit-graph.sh b/t/t5318-commit-graph.sh
index 98c69109632c2d..524d7eaa991c75 100755
--- a/t/t5318-commit-graph.sh
+++ b/t/t5318-commit-graph.sh
@@ -355,7 +355,7 @@ test_expect_success 'commit grafts invalidate commit-graph' '
 
 test_expect_success 'replace-objects invalidates commit-graph' '
 	test_when_finished rm -rf shallow &&
-	git clone --depth 2 "file://$TRASH_DIRECTORY/full" shallow &&
+	git clone --depth 2 "$TRASH_DIRECTORY_URL/full" shallow &&
 	(
 		cd shallow &&
 		git commit-graph write --reachable &&
diff --git a/t/t5510-fetch.sh b/t/t5510-fetch.sh
index ce1c23684ece38..eaa34dc37d97a5 100755
--- a/t/t5510-fetch.sh
+++ b/t/t5510-fetch.sh
@@ -981,7 +981,7 @@ test_expect_success 'fetch.writeCommitGraph with submodules' '
 	git clone dups super &&
 	(
 		cd super &&
-		git submodule add "file://$TRASH_DIRECTORY/three" &&
+		git submodule add "$TRASH_DIRECTORY_URL/three" &&
 		git commit -m "add submodule"
 	) &&
 	git clone "super" super-clone &&
@@ -1314,7 +1314,7 @@ test_expect_success 'fetching with auto-gc does not lock up' '
 	echo "$*" &&
 	false
 	EOF
-	git clone "file://$PWD" auto-gc &&
+	git clone "file://$(pwd)" auto-gc &&
 	test_commit test2 &&
 	(
 		cd auto-gc &&
diff --git a/t/t5527-fetch-odd-refs.sh b/t/t5527-fetch-odd-refs.sh
index 0de8eb5b6f8855..7b4da983c93fa3 100755
--- a/t/t5527-fetch-odd-refs.sh
+++ b/t/t5527-fetch-odd-refs.sh
@@ -23,7 +23,7 @@ test_expect_success 'setup repo with odd suffix ref' '
 '
 
 test_expect_success 'suffix ref is ignored during fetch' '
-	git clone --bare file://"$PWD" suffix &&
+	git clone --bare file://"$(pwd)" suffix &&
 	echo three >expect &&
 	git --git-dir=suffix log -1 --format=%s refs/heads/main >actual &&
 	test_cmp expect actual
diff --git a/t/t5537-fetch-shallow.sh b/t/t5537-fetch-shallow.sh
index 6588ce62264331..448b383e4fbf8b 100755
--- a/t/t5537-fetch-shallow.sh
+++ b/t/t5537-fetch-shallow.sh
@@ -236,7 +236,7 @@ test_expect_success '.git/shallow is edited by repack' '
 	git -C shallow-server checkout main &&
 
 	git clone --depth=1 --no-tags --no-single-branch \
-		"file://$PWD/shallow-server" shallow-client &&
+		"file://$(pwd)/shallow-server" shallow-client &&
 
 	: now remove the branch and fetch with prune &&
 	git -C shallow-server branch -D branch &&
diff --git a/t/t5553-set-upstream.sh b/t/t5553-set-upstream.sh
index 70e3376d31b431..3f7ad9378cc705 100755
--- a/t/t5553-set-upstream.sh
+++ b/t/t5553-set-upstream.sh
@@ -84,7 +84,7 @@ test_expect_success 'fetch --set-upstream ./does-not-exist fails with invalid ur
 
 test_expect_success 'fetch --set-upstream with valid URL sets upstream to URL' '
 	clear_config other other2 &&
-	url="file://$PWD" &&
+	url="file://$(pwd)" &&
 	git fetch --set-upstream "$url" &&
 	check_config main "$url" HEAD &&
 	check_config_missing other &&
@@ -172,7 +172,7 @@ test_expect_success 'pull --set-upstream upstream with more than one branch does
 test_expect_success 'pull --set-upstream with valid URL sets upstream to URL' '
 	clear_config main other other2 &&
 	git checkout main &&
-	url="file://$PWD" &&
+	url="file://$(pwd)" &&
 	git pull --set-upstream "$url" &&
 	check_config main "$url" HEAD &&
 	check_config_missing other &&
@@ -182,7 +182,7 @@ test_expect_success 'pull --set-upstream with valid URL sets upstream to URL' '
 test_expect_success 'pull --set-upstream with valid URL and branch sets branch' '
 	clear_config main other other2 &&
 	git checkout main &&
-	url="file://$PWD" &&
+	url="file://$(pwd)" &&
 	git pull --set-upstream "$url" main &&
 	check_config main "$url" refs/heads/main &&
 	check_config_missing other &&
diff --git a/t/t5601-clone.sh b/t/t5601-clone.sh
index d743d986c401a0..fb0842b8715730 100755
--- a/t/t5601-clone.sh
+++ b/t/t5601-clone.sh
@@ -249,14 +249,14 @@ test_expect_success 'clone respects global branch.autosetuprebase' '
 
 test_expect_success 'respect url-encoding of file://' '
 	git init x+y &&
-	git clone "file://$PWD/x+y" xy-url-1 &&
-	git clone "file://$PWD/x%2By" xy-url-2
+	git clone "file://$(pwd)/x+y" xy-url-1 &&
+	git clone "file://$(pwd)/x%2By" xy-url-2
 '
 
 test_expect_success 'do not query-string-decode + in URLs' '
 	rm -rf x+y &&
 	git init "x y" &&
-	test_must_fail git clone "file://$PWD/x+y" xy-no-plus
+	test_must_fail git clone "file://$(pwd)/x+y" xy-no-plus
 '
 
 test_expect_success 'do not respect url-encoding of non-url path' '
diff --git a/t/t5610-clone-detached.sh b/t/t5610-clone-detached.sh
index a7ec21eda5aabf..0f51f06f7c45d9 100755
--- a/t/t5610-clone-detached.sh
+++ b/t/t5610-clone-detached.sh
@@ -24,7 +24,7 @@ test_expect_success 'setup' '
 
 test_expect_success 'clone repo (detached HEAD points to branch)' '
 	git checkout main^0 &&
-	git clone "file://$PWD" detached-branch
+	git clone "file://$(pwd)" detached-branch
 '
 test_expect_success 'cloned HEAD matches' '
 	echo three >expect &&
@@ -37,7 +37,7 @@ test_expect_failure 'cloned HEAD is detached' '
 
 test_expect_success 'clone repo (detached HEAD points to tag)' '
 	git checkout two^0 &&
-	git clone "file://$PWD" detached-tag
+	git clone "file://$(pwd)" detached-tag
 '
 test_expect_success 'cloned HEAD matches' '
 	echo two >expect &&
@@ -50,7 +50,7 @@ test_expect_success 'cloned HEAD is detached' '
 
 test_expect_success 'clone repo (detached HEAD points to history)' '
 	git checkout two^ &&
-	git clone "file://$PWD" detached-history
+	git clone "file://$(pwd)" detached-history
 '
 test_expect_success 'cloned HEAD matches' '
 	echo one >expect &&
@@ -65,7 +65,7 @@ test_expect_success 'clone repo (orphan detached HEAD)' '
 	git checkout main^0 &&
 	echo four >file &&
 	git commit -a -m four &&
-	git clone "file://$PWD" detached-orphan
+	git clone "file://$(pwd)" detached-orphan
 '
 test_expect_success 'cloned HEAD matches' '
 	echo four >expect &&
diff --git a/t/t5810-proto-disable-local.sh b/t/t5810-proto-disable-local.sh
index 96a2c46e7a6bd5..624fa951e12360 100755
--- a/t/t5810-proto-disable-local.sh
+++ b/t/t5810-proto-disable-local.sh
@@ -9,7 +9,7 @@ test_expect_success 'setup repository to clone' '
 	test_commit one
 '
 
-test_proto "file://" file "file://$PWD"
+test_proto "file://" file "file://$(pwd)"
 test_proto "path" file .
 
 test_expect_success 'setup repo with dash' '
diff --git a/t/t7406-submodule-update.sh b/t/t7406-submodule-update.sh
index 3adab12091a5f0..c51d692cfae614 100755
--- a/t/t7406-submodule-update.sh
+++ b/t/t7406-submodule-update.sh
@@ -1085,7 +1085,7 @@ test_expect_success 'submodule update --quiet passes quietness to fetch with a s
 	test_when_finished "rm -rf super4 super5 super6" &&
 	git clone . super4 &&
 	(cd super4 &&
-	 git submodule add --quiet file://"$TRASH_DIRECTORY"/submodule submodule3 &&
+	 git submodule add --quiet "$TRASH_DIRECTORY_URL"/submodule submodule3 &&
 	 git commit -am "setup submodule3"
 	) &&
 	(cd submodule &&
diff --git a/t/test-lib.sh b/t/test-lib.sh
index 0fb76f7d11e840..94f7c4aaa46b4d 100644
--- a/t/test-lib.sh
+++ b/t/test-lib.sh
@@ -348,6 +348,7 @@ case "$TRASH_DIRECTORY" in
 /*) ;; # absolute path is good
  *) TRASH_DIRECTORY="$TEST_OUTPUT_DIRECTORY/$TRASH_DIRECTORY" ;;
 esac
+TRASH_DIRECTORY_URL=file://"$TRASH_DIRECTORY"
 
 # If --stress was passed, run this test repeatedly in several parallel loops.
 if test "$GIT_TEST_STRESS_STARTED" = "done"
@@ -1682,6 +1683,7 @@ Darwin)
 	test_set_prereq GREP_STRIPS_CR
 	test_set_prereq WINDOWS
 	GIT_TEST_CMP="GIT_DIR=/dev/null git diff --no-index --ignore-cr-at-eol --"
+	TRASH_DIRECTORY_URL=file://"$(cygpath -am "$TRASH_DIRECTORY")"
 	;;
 *CYGWIN*)
 	test_set_prereq POSIXPERM