diff --git a/src/basic/env-file.c b/src/basic/env-file.c
index 26470796eb..dc92b13a6f 100644
--- a/src/basic/env-file.c
+++ b/src/basic/env-file.c
@@ -209,17 +209,21 @@ static int parse_env_file_internal(
                 case DOUBLE_QUOTE_VALUE_ESCAPE:
                         state = DOUBLE_QUOTE_VALUE;
 
-                        if (c == '"') {
+                        if (strchr(SHELL_NEED_ESCAPE, c)) {
+                                /* If this is a char that needs escaping, just unescape it. */
                                 if (!GREEDY_REALLOC(value, value_alloc, n_value+2))
                                         return -ENOMEM;
-                                value[n_value++] = '"';
-                        } else if (!strchr(NEWLINE, c)) {
+                                value[n_value++] = c;
+                        } else if (c != '\n') {
+                                /* If other char than what needs escaping, keep the "\" in place, like the
+                                 * real shell does. */
                                 if (!GREEDY_REALLOC(value, value_alloc, n_value+3))
                                         return -ENOMEM;
                                 value[n_value++] = '\\';
                                 value[n_value++] = c;
                         }
 
+                        /* Escaped newlines (aka "continuation lines") are eaten up entirely */
                         break;
 
                 case COMMENT:
diff --git a/src/test/test-env-file.c b/src/test/test-env-file.c
index 47f86a5676..861238169b 100644
--- a/src/test/test-env-file.c
+++ b/src/test/test-env-file.c
@@ -2,6 +2,7 @@
 
 #include "env-file.h"
 #include "fd-util.h"
+#include "fileio.h"
 #include "fs-util.h"
 #include "macro.h"
 #include "strv.h"
@@ -132,6 +133,46 @@ static void test_load_env_file_5(void) {
         assert_se(data[2] == NULL);
 }
 
+static void test_write_and_load_env_file(void) {
+        const char *v;
+
+        /* Make sure that our writer, parser and the shell agree on what our env var files mean */
+
+        FOREACH_STRING(v,
+                       "obbardc-laptop",
+                       "obbardc\\-laptop",
+                       "obbardc-lap\\top",
+                       "obbardc-lap\\top",
+                       "obbardc-lap\\\\top",
+                       "double\"quote",
+                       "single\'quote",
+                       "dollar$dollar",
+                       "newline\nnewline") {
+                _cleanup_(unlink_and_freep) char *p = NULL;
+                _cleanup_strv_free_ char **l = NULL;
+                _cleanup_free_ char *j = NULL, *w = NULL, *cmd = NULL, *from_shell = NULL;
+                _cleanup_fclose_ FILE *f = NULL;
+                size_t sz;
+
+                assert_se(tempfn_random_child(NULL, NULL, &p) >= 0);
+
+                assert_se(j = strjoin("TEST=", v));
+                assert_se(write_env_file(p, STRV_MAKE(j)) >= 0);
+
+                assert_se(cmd = strjoin(". ", p, " && /bin/echo -n \"$TEST\""));
+                assert_se(f = popen(cmd, "re"));
+                assert_se(read_full_stream(f, &from_shell, &sz) >= 0);
+                assert_se(sz == strlen(v));
+                assert_se(streq(from_shell, v));
+
+                assert_se(load_env_file(NULL, p, &l) >= 0);
+                assert_se(strv_equal(l, STRV_MAKE(j)));
+
+                assert_se(parse_env_file(NULL, p, "TEST", &w) >= 0);
+                assert_se(streq_ptr(w, v));
+        }
+}
+
 int main(int argc, char *argv[]) {
         test_setup_logging(LOG_INFO);
 
@@ -140,4 +181,8 @@ int main(int argc, char *argv[]) {
         test_load_env_file_3();
         test_load_env_file_4();
         test_load_env_file_5();
+
+        test_write_and_load_env_file();
+
+        return 0;
 }
diff --git a/src/test/test-fileio.c b/src/test/test-fileio.c
index 95dcd4fdb1..9c0b3533c2 100644
--- a/src/test/test-fileio.c
+++ b/src/test/test-fileio.c
@@ -151,6 +151,18 @@ static void test_parse_env_file(void) {
         assert_se(r >= 0);
 }
 
+static void test_one_shell_var(const char *file, const char *variable, const char *value) {
+        _cleanup_free_ char *cmd = NULL, *from_shell = NULL;
+        _cleanup_fclose_ FILE *f = NULL;
+        size_t sz;
+
+        assert_se(cmd = strjoin(". ", file, " && /bin/echo -n \"$", variable, "\""));
+        assert_se(f = popen(cmd, "re"));
+        assert_se(read_full_stream(f, &from_shell, &sz) >= 0);
+        assert_se(sz == strlen(value));
+        assert_se(streq(from_shell, value));
+}
+
 static void test_parse_multiline_env_file(void) {
         _cleanup_(unlink_tempfilep) char
                 t[] = "/tmp/test-fileio-in-XXXXXX",
@@ -162,8 +174,8 @@ static void test_parse_multiline_env_file(void) {
 
         assert_se(fmkostemp_safe(t, "w", &f) == 0);
         fputs("one=BAR\\\n"
-              "    VAR\\\n"
-              "\tGAR\n"
+              "\\ \\ \\ \\ VAR\\\n"
+              "\\\tGAR\n"
               "#comment\n"
               "two=\"bar\\\n"
               "    var\\\n"
@@ -173,9 +185,13 @@ static void test_parse_multiline_env_file(void) {
               "    var \\\n"
               "\tgar \"\n", f);
 
-        fflush(f);
+        assert_se(fflush_and_check(f) >= 0);
         fclose(f);
 
+        test_one_shell_var(t, "one", "BAR    VAR\tGAR");
+        test_one_shell_var(t, "two", "bar    var\tgar");
+        test_one_shell_var(t, "tri", "bar     var \tgar ");
+
         r = load_env_file(NULL, t, &a);
         assert_se(r >= 0);