diff --git a/src/basic/os-util.c b/src/basic/os-util.c
index dbd067fd44..985d89bc7e 100644
--- a/src/basic/os-util.c
+++ b/src/basic/os-util.c
@@ -61,6 +61,39 @@ bool image_name_is_valid(const char *s) {
         return true;
 }
 
+int path_extract_image_name(const char *path, char **ret) {
+        _cleanup_free_ char *fn = NULL;
+        int r;
+
+        assert(path);
+        assert(ret);
+
+        /* Extract last component from path, without any "/" suffixes. */
+        r = path_extract_filename(path, &fn);
+        if (r < 0)
+                return r;
+
+        if (r != O_DIRECTORY) {
+                /* Chop off any image suffixes we recognize (unless we already know this must refer to some dir */
+                FOREACH_STRING(suffix, ".sysext.raw", ".confext.raw", ".raw") {
+                        char *m = endswith(fn, suffix);
+                        if (m) {
+                                *m = 0;
+                                break;
+                        }
+                }
+        }
+
+        /* Truncate the version/counting suffixes */
+        fn[strcspn(fn, "_+")] = 0;
+
+        if (!image_name_is_valid(fn))
+                return -EINVAL;
+
+        *ret = TAKE_PTR(fn);
+        return 0;
+}
+
 int path_is_extension_tree(ImageClass image_class, const char *path, const char *extension, bool relax_extension_release_check) {
         int r;
 
@@ -230,9 +263,25 @@ int open_extension_release_at(
                         continue;
                 }
 
-                if (!relax_extension_release_check &&
-                    extension_release_strict_xattr_value(fd, dir_path, de->d_name) != 0)
-                        continue;
+                if (!relax_extension_release_check) {
+                        _cleanup_free_ char *base_image_name = NULL, *base_extension = NULL;
+
+                        r = path_extract_image_name(image_name, &base_image_name);
+                        if (r < 0) {
+                                log_debug_errno(r, "Failed to extract image name from %s/%s, ignoring: %m", dir_path, de->d_name);
+                                continue;
+                        }
+
+                        r = path_extract_image_name(extension, &base_extension);
+                        if (r < 0) {
+                                log_debug_errno(r, "Failed to extract image name from %s, ignoring: %m", extension);
+                                continue;
+                        }
+
+                        if (!streq(base_image_name, base_extension) &&
+                            extension_release_strict_xattr_value(fd, dir_path, image_name) != 0)
+                                continue;
+                }
 
                 /* We already found what we were looking for, but there's another candidate? We treat this as
                  * an error, as we want to enforce that there are no ambiguities in case we are in the
diff --git a/src/basic/os-util.h b/src/basic/os-util.h
index 7cee3dd119..f6a12a3fb1 100644
--- a/src/basic/os-util.h
+++ b/src/basic/os-util.h
@@ -25,6 +25,7 @@ ImageClass image_class_from_string(const char *s) _pure_;
  * in accordance with the OS extension specification, rather than for /usr/lib/ or /etc/os-release. */
 
 bool image_name_is_valid(const char *s) _pure_;
+int path_extract_image_name(const char *path, char **ret);
 
 int path_is_extension_tree(ImageClass image_class, const char *path, const char *extension, bool relax_extension_release_check);
 static inline int path_is_os_tree(const char *path) {
diff --git a/src/portable/portable.c b/src/portable/portable.c
index a3bec83f0d..60dc98c5ba 100644
--- a/src/portable/portable.c
+++ b/src/portable/portable.c
@@ -1664,9 +1664,8 @@ int portable_attach(
         return 0;
 }
 
-static bool marker_matches_images(const char *marker, const char *name_or_path, char **extension_image_paths) {
+static bool marker_matches_images(const char *marker, const char *name_or_path, char **extension_image_paths, bool match_all) {
         _cleanup_strv_free_ char **root_and_extensions = NULL;
-        const char *a;
         int r;
 
         assert(marker);
@@ -1676,7 +1675,9 @@ static bool marker_matches_images(const char *marker, const char *name_or_path,
          * list of images/paths. We enforce strict 1:1 matching, so that we are sure
          * we are detaching exactly what was attached.
          * For each image, starting with the root, we look for a token in the marker,
-         * and return a negative answer on any non-matching combination. */
+         * and return a negative answer on any non-matching combination.
+         * If a partial match is allowed, then return immediately once it is found, otherwise
+         * ensure that everything matches. */
 
         root_and_extensions = strv_new(name_or_path);
         if (!root_and_extensions)
@@ -1686,70 +1687,33 @@ static bool marker_matches_images(const char *marker, const char *name_or_path,
         if (r < 0)
                 return r;
 
-        STRV_FOREACH(image_name_or_path, root_and_extensions) {
-                _cleanup_free_ char *image = NULL;
+        /* Ensure the number of images passed matches the number of images listed in the marker */
+        while (!isempty(marker))
+                STRV_FOREACH(image_name_or_path, root_and_extensions) {
+                        _cleanup_free_ char *image = NULL, *base_image = NULL, *base_image_name_or_path = NULL;
 
-                r = extract_first_word(&marker, &image, ":", EXTRACT_UNQUOTE|EXTRACT_RETAIN_ESCAPE);
-                if (r < 0)
-                        return log_debug_errno(r, "Failed to parse marker: %s", marker);
-                if (r == 0)
-                        return false;
-
-                a = last_path_component(image);
-
-                if (image_name_is_valid(*image_name_or_path)) {
-                        const char *e, *underscore;
-
-                        /* We shall match against an image name. In that case let's compare the last component, and optionally
-                        * allow either a suffix of ".raw" or a series of "/".
-                        * But allow matching on a different version of the same image, when a "_" is used as a separator. */
-                        underscore = strchr(*image_name_or_path, '_');
-                        if (underscore) {
-                                if (strneq(a, *image_name_or_path, underscore - *image_name_or_path))
-                                        continue;
-                                return false;
-                        }
-
-                        e = startswith(a, *image_name_or_path);
-                        if (!e)
+                        r = extract_first_word(&marker, &image, ":", EXTRACT_UNQUOTE|EXTRACT_RETAIN_ESCAPE);
+                        if (r < 0)
+                                return log_debug_errno(r, "Failed to parse marker: %s", marker);
+                        if (r == 0)
                                 return false;
 
-                        if(!(e[strspn(e, "/")] == 0 || streq(e, ".raw")))
-                                return false;
-                } else {
-                        const char *b, *underscore;
-                        size_t l;
+                        r = path_extract_image_name(image, &base_image);
+                        if (r < 0)
+                                return log_debug_errno(r, "Failed to extract image name from %s, ignoring: %m", image);
 
-                        /* We shall match against a path. Let's ignore any prefix here though, as often there are many ways to
-                         * reach the same file. However, in this mode, let's validate any file suffix.
-                         * But also ensure that we don't fail if both components don't have a '/' at all
-                         * (strcspn returns the full length of the string in that case, which might not
-                         * match as the versions might differ). */
+                        r = path_extract_image_name(*image_name_or_path, &base_image_name_or_path);
+                        if (r < 0)
+                                return log_debug_errno(r, "Failed to extract image name from %s, ignoring: %m", *image_name_or_path);
 
-                        l = strcspn(a, "/");
-                        b = last_path_component(*image_name_or_path);
-
-                        if ((a[l] != '/') != !strchr(b, '/')) /* One is a directory, the other is not */
-                                return false;
-
-                        if (a[l] != 0 && strcspn(b, "/") != l)
-                                return false;
-
-                        underscore = strchr(b, '_');
-                        if (underscore)
-                                l = underscore - b;
-                        else { /* Either component could be versioned */
-                                underscore = strchr(a, '_');
-                                if (underscore)
-                                        l = underscore - a;
-                        }
-
-                        if (!strneq(a, b, l))
-                                return false;
+                        if (!streq(base_image, base_image_name_or_path)) {
+                                if (match_all)
+                                        return false;
+                        } else if (!match_all)
+                                return true;
                 }
-        }
 
-        return true;
+        return match_all;
 }
 
 static int test_chroot_dropin(
@@ -1804,7 +1768,9 @@ static int test_chroot_dropin(
         if (!name_or_path)
                 r = true;
         else
-                r = marker_matches_images(marker, name_or_path, extension_image_paths);
+                /* When detaching we want to match exactly on all images, but when inspecting we only need
+                 * to get the state of one component */
+                r = marker_matches_images(marker, name_or_path, extension_image_paths, ret_marker != NULL);
 
         if (ret_marker)
                 *ret_marker = TAKE_PTR(marker);
diff --git a/test/units/testsuite-29.sh b/test/units/testsuite-29.sh
index d40cef2551..7af0ed4578 100755
--- a/test/units/testsuite-29.sh
+++ b/test/units/testsuite-29.sh
@@ -139,6 +139,19 @@ grep -q -F "LogExtraFields=PORTABLE_EXTENSION_NAME_AND_VERSION=app" /run/systemd
 
 portablectl detach --now --runtime --extension /usr/share/app0.raw /usr/share/minimal_1.raw app0
 
+# Ensure versioned images are accepted without needing to use --force to override the extension-release
+# matching
+
+cp /usr/share/app0.raw /tmp/app0_1.0.raw
+portablectl "${ARGS[@]}" attach --now --runtime --extension /tmp/app0_1.0.raw /usr/share/minimal_0.raw app0
+
+systemctl is-active app0.service
+status="$(portablectl is-attached --extension app0_1 minimal_0)"
+[[ "${status}" == "running-runtime" ]]
+
+portablectl detach --now --runtime --extension /tmp/app0_1.0.raw /usr/share/minimal_1.raw app0
+rm -f /tmp/app0_1.0.raw
+
 portablectl "${ARGS[@]}" attach --now --runtime --extension /usr/share/app1.raw /usr/share/minimal_0.raw app1
 
 systemctl is-active app1.service
@@ -211,6 +224,36 @@ test -f /run/systemd/system.attached/app0.service
 test -L /run/systemd/system.attached/app0.service.d/10-profile.conf
 portablectl detach --runtime --extension /usr/share/app0.raw /usr/share/minimal_0.raw app0
 
+# Ensure that when two portables share the same base image, removing one doesn't remove the other too
+
+portablectl "${ARGS[@]}" attach --runtime --extension /usr/share/app0.raw /usr/share/minimal_0.raw app0
+portablectl "${ARGS[@]}" attach --runtime --extension /usr/share/app1.raw /usr/share/minimal_0.raw app1
+
+status="$(portablectl is-attached --extension app0 minimal_0)"
+[[ "${status}" == "attached-runtime" ]]
+status="$(portablectl is-attached --extension app1 minimal_0)"
+[[ "${status}" == "attached-runtime" ]]
+
+(! portablectl detach --runtime /usr/share/minimal_0.raw app)
+
+status="$(portablectl is-attached --extension app0 minimal_0)"
+[[ "${status}" == "attached-runtime" ]]
+status="$(portablectl is-attached --extension app1 minimal_0)"
+[[ "${status}" == "attached-runtime" ]]
+
+# Ensure 'portablectl list' shows the correct status for both images
+portablectl list
+portablectl list | grep -F "minimal_0" | grep -q -F "attached-runtime"
+portablectl list | grep -F "app0" | grep -q -F "attached-runtime"
+portablectl list | grep -F "app1" | grep -q -F "attached-runtime"
+
+portablectl detach --runtime --extension /usr/share/app0.raw /usr/share/minimal_0.raw app
+
+status="$(portablectl is-attached --extension app1 minimal_0)"
+[[ "${status}" == "attached-runtime" ]]
+
+portablectl detach --runtime --extension /usr/share/app1.raw /usr/share/minimal_0.raw app
+
 # portablectl also works with directory paths rather than images
 
 mkdir /tmp/rootdir /tmp/app0 /tmp/app1 /tmp/overlay /tmp/os-release-fix /tmp/os-release-fix/etc