diff --git a/src/liblibc/lib.rs b/src/liblibc/lib.rs
index 5cd806dc9e3f3..c4d2dc838942a 100644
--- a/src/liblibc/lib.rs
+++ b/src/liblibc/lib.rs
@@ -3920,6 +3920,8 @@ pub mod consts {
             pub const _SC_XBS5_ILP32_OFFBIG : c_int = 126;
             pub const _SC_XBS5_LPBIG_OFFBIG : c_int = 128;
 
+            pub const _PC_NAME_MAX: c_int = 3;
+            pub const _PC_PATH_MAX: c_int = 4;
         }
         #[cfg(target_os = "nacl")]
         pub mod sysconf {
@@ -3928,6 +3930,9 @@ pub mod consts {
             pub static _SC_SENDMSG_MAX_SIZE : c_int = 0;
             pub static _SC_NPROCESSORS_ONLN : c_int = 1;
             pub static _SC_PAGESIZE : c_int = 2;
+
+            pub const _PC_NAME_MAX: c_int = 3;
+            pub const _PC_PATH_MAX: c_int = 4;
         }
 
         #[cfg(target_os = "android")]
@@ -3963,6 +3968,9 @@ pub mod consts {
             pub const _SC_STREAM_MAX : c_int = 27;
             pub const _SC_TZNAME_MAX : c_int = 28;
             pub const _SC_PAGESIZE : c_int = 39;
+
+            pub const _PC_NAME_MAX: c_int = 4;
+            pub const _PC_PATH_MAX: c_int = 5;
         }
     }
 
@@ -4433,6 +4441,9 @@ pub mod consts {
             pub const _SC_SEM_VALUE_MAX : c_int = 50;
             pub const _SC_SIGQUEUE_MAX : c_int = 51;
             pub const _SC_TIMER_MAX : c_int = 52;
+
+            pub const _PC_NAME_MAX: c_int = 4;
+            pub const _PC_PATH_MAX: c_int = 5;
         }
     }
 
@@ -4868,6 +4879,9 @@ pub mod consts {
             pub const _SC_SYNCHRONIZED_IO : c_int = 75;
             pub const _SC_TIMER_MAX : c_int = 93;
             pub const _SC_TIMERS : c_int = 94;
+
+            pub const _PC_NAME_MAX: c_int = 4;
+            pub const _PC_PATH_MAX: c_int = 5;
         }
     }
 
@@ -5379,6 +5393,9 @@ pub mod consts {
             pub const _SC_TRACE_SYS_MAX : c_int = 129;
             pub const _SC_TRACE_USER_EVENT_MAX : c_int = 130;
             pub const _SC_PASS_MAX : c_int = 131;
+
+            pub const _PC_NAME_MAX: c_int = 4;
+            pub const _PC_PATH_MAX: c_int = 5;
         }
     }
 }
@@ -5835,8 +5852,6 @@ pub mod funcs {
             use types::os::arch::posix88::{gid_t, off_t, pid_t};
             use types::os::arch::posix88::{ssize_t, uid_t};
 
-            pub const _PC_NAME_MAX: c_int = 4;
-
             #[cfg(not(target_os = "nacl"))]
             extern {
                 pub fn access(path: *const c_char, amode: c_int) -> c_int;
diff --git a/src/libstd/sys/unix/fs.rs b/src/libstd/sys/unix/fs.rs
index cbbdd223dc2b9..0eebe5af9197d 100644
--- a/src/libstd/sys/unix/fs.rs
+++ b/src/libstd/sys/unix/fs.rs
@@ -376,6 +376,11 @@ impl fmt::Debug for File {
 
         #[cfg(target_os = "macos")]
         fn get_path(fd: c_int) -> Option<PathBuf> {
+            // FIXME: The use of PATH_MAX is generally not encouraged, but it
+            // is inevitable in this case because OS X defines `fcntl` with
+            // `F_GETPATH` in terms of `MAXPATHLEN`, and there are no
+            // alternatives. If a better method is invented, it should be used
+            // instead.
             let mut buf = vec![0;libc::PATH_MAX as usize];
             let n = unsafe { libc::fcntl(fd, libc::F_GETPATH, buf.as_ptr()) };
             if n == -1 {
@@ -383,6 +388,7 @@ impl fmt::Debug for File {
             }
             let l = buf.iter().position(|&c| c == 0).unwrap();
             buf.truncate(l as usize);
+            buf.shrink_to_fit();
             Some(PathBuf::from(OsString::from_vec(buf)))
         }
 
@@ -466,18 +472,27 @@ pub fn rmdir(p: &Path) -> io::Result<()> {
 pub fn readlink(p: &Path) -> io::Result<PathBuf> {
     let c_path = try!(cstr(p));
     let p = c_path.as_ptr();
-    let mut len = unsafe { libc::pathconf(p as *mut _, libc::_PC_NAME_MAX) };
-    if len < 0 {
-        len = 1024; // FIXME: read PATH_MAX from C ffi?
-    }
-    let mut buf: Vec<u8> = Vec::with_capacity(len as usize);
-    unsafe {
-        let n = try!(cvt({
-            libc::readlink(p, buf.as_ptr() as *mut c_char, len as size_t)
-        }));
-        buf.set_len(n as usize);
+
+    let mut buf = Vec::with_capacity(256);
+
+    loop {
+        let buf_read = try!(cvt(unsafe {
+            libc::readlink(p, buf.as_mut_ptr() as *mut _, buf.capacity() as libc::size_t)
+        })) as usize;
+
+        unsafe { buf.set_len(buf_read); }
+
+        if buf_read != buf.capacity() {
+            buf.shrink_to_fit();
+
+            return Ok(PathBuf::from(OsString::from_vec(buf)));
+        }
+
+        // Trigger the internal buffer resizing logic of `Vec` by requiring
+        // more space than the current capacity. The length is guaranteed to be
+        // the same as the capacity due to the if statement above.
+        buf.reserve(1);
     }
-    Ok(PathBuf::from(OsString::from_vec(buf)))
 }
 
 pub fn symlink(src: &Path, dst: &Path) -> io::Result<()> {
@@ -514,15 +529,15 @@ pub fn lstat(p: &Path) -> io::Result<FileAttr> {
 
 pub fn canonicalize(p: &Path) -> io::Result<PathBuf> {
     let path = try!(CString::new(p.as_os_str().as_bytes()));
-    let mut buf = vec![0u8; 16 * 1024];
+    let buf;
     unsafe {
-        let r = c::realpath(path.as_ptr(), buf.as_mut_ptr() as *mut _);
+        let r = c::realpath(path.as_ptr(), ptr::null_mut());
         if r.is_null() {
             return Err(io::Error::last_os_error())
         }
+        buf = CStr::from_ptr(r).to_bytes().to_vec();
+        libc::free(r as *mut _);
     }
-    let p = buf.iter().position(|i| *i == 0).unwrap();
-    buf.truncate(p);
     Ok(PathBuf::from(OsString::from_vec(buf)))
 }
 
diff --git a/src/libstd/sys/unix/os.rs b/src/libstd/sys/unix/os.rs
index 2b6b50a1a56d7..fa31ac682d40b 100644
--- a/src/libstd/sys/unix/os.rs
+++ b/src/libstd/sys/unix/os.rs
@@ -30,7 +30,6 @@ use sys::c;
 use sys::fd;
 use vec;
 
-const GETCWD_BUF_BYTES: usize = 2048;
 const TMPBUF_SZ: usize = 128;
 
 /// Returns the platform-specific value of errno
@@ -94,11 +93,9 @@ pub fn error_string(errno: i32) -> String {
 }
 
 pub fn getcwd() -> io::Result<PathBuf> {
-    let mut buf = Vec::new();
-    let mut n = GETCWD_BUF_BYTES;
+    let mut buf = Vec::with_capacity(512);
     loop {
         unsafe {
-            buf.reserve(n);
             let ptr = buf.as_mut_ptr() as *mut libc::c_char;
             if !libc::getcwd(ptr, buf.capacity() as libc::size_t).is_null() {
                 let len = CStr::from_ptr(buf.as_ptr() as *const libc::c_char).to_bytes().len();
@@ -111,7 +108,12 @@ pub fn getcwd() -> io::Result<PathBuf> {
                     return Err(error);
                 }
             }
-            n *= 2;
+
+            // Trigger the internal buffer resizing logic of `Vec` by requiring
+            // more space than the current capacity.
+            let cap = buf.capacity();
+            buf.set_len(cap);
+            buf.reserve(1);
         }
     }
 }
diff --git a/src/rt/rust_builtin.c b/src/rt/rust_builtin.c
index 945057f86122e..37ce30d7066f7 100644
--- a/src/rt/rust_builtin.c
+++ b/src/rt/rust_builtin.c
@@ -341,7 +341,11 @@ const char * rust_current_exe()
   char **paths;
   size_t sz;
   int i;
-  char buf[2*PATH_MAX], exe[2*PATH_MAX];
+  /* If `PATH_MAX` is defined on the platform, `realpath` will truncate the
+   * resolved path up to `PATH_MAX`. While this can make the resolution fail if
+   * the executable is placed in a deep path, the usage of a buffer whose
+   * length depends on `PATH_MAX` is still memory safe. */
+  char buf[2*PATH_MAX], exe[PATH_MAX];
 
   if (self != NULL)
     return self;