diff --git a/src/search.cpp b/src/search.cpp
index daa6d27..3f0a3a9 100644
--- a/src/search.cpp
+++ b/src/search.cpp
@@ -69,9 +69,41 @@ namespace search {
             return out;
         }
 
-        const std::vector<fs::path> search_paths() {
+        /// @brief Build a combination of all prefixes, subdirs, and name-like paths
+        /// @param roots the prefix roots
+        /// @param name the name of the package to find
+        /// @return all of the search paths combined into concrete instances
+        std::vector<fs::path> expand_search_paths(const std::vector<fs::path> & roots, std::string_view name) {
             // TODO: Windows paths
             // TODO: MacOS paths
+            const std::vector<fs::path> segments{platform::libdir(), "share"};
+            std::vector<fs::path> paths;
+
+            for (auto && root : roots) {
+                for (auto && segment : segments) {
+                    if (const fs::path subdir = root / segment / "cps"; fs::is_directory(subdir)) {
+                        paths.emplace_back(subdir);
+                        if (const fs::path namedir = subdir / name; fs::is_directory(namedir)) {
+                            paths.emplace_back(namedir);
+                            for (const fs::path & name_subdir : fs::directory_iterator(namedir)) {
+                                if (fs::is_directory(name_subdir)) {
+                                    paths.emplace_back(name_subdir);
+                                }
+                            }
+                        }
+                    }
+                }
+            }
+
+            return paths;
+        }
+
+        /// @brief create concrete search paths for a specific package
+        /// @param name the name of the package
+        /// @return a vector of those paths
+        std::vector<fs::path> search_paths(std::string_view name) {
+
+            // Build all of the roots to search
             std::vector<fs::path> roots;
             if (const char * env_c = std::getenv("CPS_PATH")) {
                 auto && env = utils::split(env_c);
@@ -79,12 +111,7 @@ namespace search {
             }
             roots.emplace_back("/usr");
 
-            std::vector<fs::path> paths;
-            for (auto && root : roots) {
-                paths.emplace_back(root / platform::libdir() / "cps");
-                paths.emplace_back(root / "share/cps");
-            }
-            return paths;
+            return expand_search_paths(roots, name);
         }
 
         /// @brief Find all possible paths for a given CPS name
@@ -97,19 +124,10 @@ namespace search {
             }
 
             // TODO: Need something like pkgconf's --personality option
-            // TODO: we likely either need to return all possible files, or load
-            // a file
-            // TODO: what to do about finding multiple versions of the same
-            // dependency?
-            auto && paths = search_paths();
+            auto && paths = search_paths(name);
             std::vector<fs::path> found{};
             for (auto && dir : paths) {
-                // TODO: <prefix>/<libdir>/cps/<name-like>/
-                // TODO: <prefix>/share/cps/<name-like>/
-                // TODO: <prefix>/share/cps/
-
                 if (fs::is_directory(dir)) {
-                    // TODO: <name-like>
                     const fs::path file = dir / fmt::format("{}.cps", name);
                     if (fs::is_regular_file(file)) {
                         found.push_back(file);
@@ -262,18 +280,31 @@ namespace search {
             }
         }
 
-        fs::path calculate_prefix(const fs::path & path) {
+        fs::path calculate_prefix(const fs::path & path, std::string_view name) {
             // TODO: Windows
-            // TODO: /cps/<name-like>
+            // TODO: Mac
+
             std::vector<std::string> split = utils::split(std::string{path}, "/");
+            // If the path ends in "/" then an empty string will be placed at
+            // the end of the split paths
             if (split.back() == "") {
                 split.pop_back();
             }
+            // If split ends in name, ex: /usr/lib/cps/name/
+            if (split.back() == name) {
+                split.pop_back();
+            }
+            // If split ends in name/*, ex: /usr/lib/cps/name/*
+            // Then drop both the */ and the name/
+            if (*(split.end() - 2) == name) {
+                split.pop_back();
+                split.pop_back();
+            }
             if (split.back() == "cps") {
                 split.pop_back();
             }
-            // Match only share or libdir, but not potentially an odd situation
-            // like /opt/share/libdir/
+            // Match only share or libdir, but not a potential odd situation
+            // like `/opt/share/libdir/`
             if (split.back() == "share" || split.back() == platform::libdir()) {
                 split.pop_back();
             }
@@ -352,7 +383,7 @@ namespace search {
                 // TODO: Windows…
                 auto && split = utils::split(s, "/");
                 if (split[0] == "@prefix@") {
-                    fs::path p = calculate_prefix(node->data.package.cps_path);
+                    fs::path p = calculate_prefix(node->data.package.cps_path, node->data.package.name);
                     for (auto it = split.begin() + 1; it != split.end(); ++it) {
                         p /= *it;
                     }
diff --git a/tests/cases.toml b/tests/cases.toml
index 4a9d0f5..c3e37ae 100644
--- a/tests/cases.toml
+++ b/tests/cases.toml
@@ -77,7 +77,19 @@
   expected = "-I/sentinel/err -l/sentinel/lib/libfoo.a"
 
 [[case]]
-  name = "prefix calculated"
+  name = "prefix calculated (found in root)"
+  cps = "cps-path-not-set-root"
+  args = ["--cflags-only-I", "--libs-only-l"]
+  expected = "-I{prefix}/err -l{prefix}/lib/libfoo.a"
+
+[[case]]
+  name = "prefix calculated (found in root/name)"
+  cps = "cps-path-not-set-subdir"
+  args = ["--cflags-only-I", "--libs-only-l"]
+  expected = "-I{prefix}/err -l{prefix}/lib/libfoo.a"
+
+[[case]]
+  name = "prefix calculated (root/name/*/)"
   cps = "cps-path-not-set"
   args = ["--cflags-only-I", "--libs-only-l"]
   expected = "-I{prefix}/err -l{prefix}/lib/libfoo.a"
diff --git a/tests/cases/lib/cps/cps-path-not-set-root.cps b/tests/cases/lib/cps/cps-path-not-set-root.cps
new file mode 100644
index 0000000..a1b36cb
--- /dev/null
+++ b/tests/cases/lib/cps/cps-path-not-set-root.cps
@@ -0,0 +1,13 @@
+{
+    "Name": "cps-path-not-set-root",
+    "Cps-Version": "0.9.0",
+    "Version": "1.0.0",
+    "Components": {
+        "default": {
+            "Type": "archive",
+            "Includes": {"C": ["@prefix@/err"]},
+            "Location": "@prefix@/lib/libfoo.a"
+        }
+    },
+    "Default-Components": ["default"]
+}
\ No newline at end of file
diff --git a/tests/cases/lib/cps/cps-path-not-set-subdir/cps-path-not-set-subdir.cps b/tests/cases/lib/cps/cps-path-not-set-subdir/cps-path-not-set-subdir.cps
new file mode 100644
index 0000000..336884d
--- /dev/null
+++ b/tests/cases/lib/cps/cps-path-not-set-subdir/cps-path-not-set-subdir.cps
@@ -0,0 +1,15 @@
+{
+    "Name": "cps-path-not-set-subdir",
+    "Cps-Version": "0.9.0",
+    "Version": "1.0.0",
+    "Components": {
+        "default": {
+            "Type": "archive",
+            "Includes": {"C": ["@prefix@/err"]},
+            "Location": "@prefix@/lib/libfoo.a"
+        }
+    },
+    "Default-Components": ["default"]
+}
+
+
diff --git a/tests/cases/lib/cps/cps-path-not-set.cps b/tests/cases/lib/cps/cps-path-not-set/foo/cps-path-not-set.cps
similarity index 100%
rename from tests/cases/lib/cps/cps-path-not-set.cps
rename to tests/cases/lib/cps/cps-path-not-set/foo/cps-path-not-set.cps
diff --git a/tests/cases/lib/cps/diamond.cps b/tests/cases/lib/cps/diamond/diamond.cps
similarity index 100%
rename from tests/cases/lib/cps/diamond.cps
rename to tests/cases/lib/cps/diamond/diamond.cps