diff --git a/CHANGELOG.md b/CHANGELOG.md
index 3795d4a..9d590a5 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -22,6 +22,9 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
     * Add support for hosting arbitrary files
         * Content type of file is set if provided when uploading file
     * Support removing entries
+* Landerctl
+    * Replaced old Bash script with Libcurl-based application
+    * Supporting posting redirects, pastes & arbitrarily large files
 
 ## [0.1.0](https://git.rustybever.be/Chewing_Bever/lander/src/tag/0.1.0)
 
diff --git a/landerctl/include/landerctl.h b/landerctl/include/landerctl.h
index 7e01ed2..28a231a 100644
--- a/landerctl/include/landerctl.h
+++ b/landerctl/include/landerctl.h
@@ -32,11 +32,28 @@ typedef enum landerctl_mode {
   landerctl_mode_file,
 } landerctl_mode;
 
-struct curl_slist *landerctl_set_common(const landerctl_cfg *cfg, CURL *curl,
-                                        landerctl_mode mode, bool secure,
-                                        const char *key);
-void landerctl_post_short(CURL *curl, const char *url);
-void landerctl_post_paste(CURL *curl, const char *path);
-void landerctl_post_file(CURL *curl, const char *path);
+typedef enum landerctl_err {
+  landerctl_err_ok = 0,
+  landerctl_err_not_found
+} landerctl_err;
+
+typedef struct landerctl_ctx {
+  landerctl_cfg cfg;
+  landerctl_mode mode;
+  bool secure;
+  bool verbose;
+  const char *arg;
+  const char *key;
+  CURL *curl;
+  struct curl_slist *headers;
+  FILE *data_file;
+} landerctl_ctx;
+
+const char *landerctl_err_msg(landerctl_err err);
+
+void landerctl_set_common(landerctl_ctx *ctx);
+landerctl_err landerctl_post_short(landerctl_ctx *ctx);
+landerctl_err landerctl_post_paste(landerctl_ctx *ctx);
+landerctl_err landerctl_post_file(landerctl_ctx *ctx);
 
 #endif
diff --git a/landerctl/src/main.c b/landerctl/src/main.c
index a88d0cc..7805635 100644
--- a/landerctl/src/main.c
+++ b/landerctl/src/main.c
@@ -13,10 +13,10 @@ const char *default_cfg_path = ".landerrc";
 const char *usage = "%s [-SPFsv] arg [key]\n";
 
 int main(int argc, char **argv) {
-  landerctl_cfg cfg;
+  landerctl_ctx ctx = {0};
   char *err_msg = NULL;
 
-  switch (landerctl_cfg_parse(&cfg, default_cfg_path)) {
+  switch (landerctl_cfg_parse(&ctx.cfg, default_cfg_path)) {
   case landerctl_cfg_err_ok:
     break;
   case landerctl_cfg_err_not_found:
@@ -38,26 +38,23 @@ int main(int argc, char **argv) {
   opterr = 0;
 
   int c;
-  landerctl_mode mode = landerctl_mode_none;
-  bool secure = false;
-  bool verbose = false;
 
   while ((c = getopt(argc, argv, "SPFsv")) != -1) {
     switch (c) {
     case 'S':
-      mode = landerctl_mode_short;
+      ctx.mode = landerctl_mode_short;
       break;
     case 'P':
-      mode = landerctl_mode_paste;
+      ctx.mode = landerctl_mode_paste;
       break;
     case 'F':
-      mode = landerctl_mode_file;
+      ctx.mode = landerctl_mode_file;
       break;
     case 's':
-      secure = true;
+      ctx.secure = true;
       break;
     case 'v':
-      verbose = true;
+      ctx.verbose = true;
       break;
     case '?':
       printf(usage, argv[0]);
@@ -65,7 +62,7 @@ int main(int argc, char **argv) {
     }
   }
 
-  if (mode == landerctl_mode_none) {
+  if (ctx.mode == landerctl_mode_none) {
     printf("No mode specified.\n\n");
     printf(usage, argv[0]);
     exit(2);
@@ -76,33 +73,49 @@ int main(int argc, char **argv) {
     exit(2);
   }
 
-  const char *arg = argv[optind];
-  const char *key = argc - optind == 2 ? argv[optind + 1] : NULL;
+  ctx.arg = argv[optind];
+  ctx.key = argc - optind == 2 ? argv[optind + 1] : NULL;
 
   curl_global_init(CURL_GLOBAL_ALL);
-  CURL *curl = curl_easy_init();
+  ctx.curl = curl_easy_init();
 
-  if (curl == NULL) {
+  if (ctx.curl == NULL) {
     exit(255);
   }
 
-  struct curl_slist *list = landerctl_set_common(&cfg, curl, mode, secure, key);
+  landerctl_set_common(&ctx);
+  landerctl_err res;
 
-  switch (mode) {
+  switch (ctx.mode) {
   case landerctl_mode_short:
-    landerctl_post_short(curl, arg);
+    res = landerctl_post_short(&ctx);
     break;
+  case landerctl_mode_paste:
+    res = landerctl_post_paste(&ctx);
+    break;
+  case landerctl_mode_file:
+    res = landerctl_post_file(&ctx);
+    break;
+  default:
+    return 7;
   }
 
-  if (verbose) {
-    curl_easy_setopt(curl, CURLOPT_VERBOSE, 1L);
+  if (res != landerctl_err_ok) {
+    printf("%s\n", landerctl_err_msg(res));
+    exit(6);
   }
 
+  if (ctx.verbose) {
+    curl_easy_setopt(ctx.curl, CURLOPT_VERBOSE, 1L);
+  }
+
+  curl_easy_setopt(ctx.curl, CURLOPT_HTTPHEADER, ctx.headers);
+
   int exit_code = 0;
 
-  if (curl_easy_perform(curl) == CURLE_OK) {
+  if (curl_easy_perform(ctx.curl) == CURLE_OK) {
     long response_code;
-    curl_easy_getinfo(curl, CURLINFO_RESPONSE_CODE, &response_code);
+    curl_easy_getinfo(ctx.curl, CURLINFO_RESPONSE_CODE, &response_code);
 
     if (response_code < 200 || response_code > 299) {
       fprintf(stderr, "HTTP status code %li\n", response_code);
@@ -110,9 +123,9 @@ int main(int argc, char **argv) {
     } else {
       struct curl_header *location_header;
 
-      if (curl_easy_header(curl, "Location", 0, CURLH_HEADER, -1,
+      if (curl_easy_header(ctx.curl, "Location", 0, CURLH_HEADER, -1,
                            &location_header) == CURLHE_OK) {
-        printf("%s%s\n", cfg.server_url, location_header->value);
+        printf("%s%s\n", ctx.cfg.server_url, location_header->value);
       } else {
         fprintf(stderr, "Server returned a 2xx without a Location header.\n");
         exit_code = 5;
@@ -123,8 +136,12 @@ int main(int argc, char **argv) {
     exit_code = 4;
   }
 
-  curl_easy_cleanup(curl);
-  curl_slist_free_all(list);
+  curl_easy_cleanup(ctx.curl);
+  curl_slist_free_all(ctx.headers);
+
+  if (ctx.data_file != NULL) {
+    fclose(ctx.data_file);
+  }
 
   return exit_code;
 
diff --git a/landerctl/src/post.c b/landerctl/src/post.c
index c0dd653..76e5b04 100644
--- a/landerctl/src/post.c
+++ b/landerctl/src/post.c
@@ -1,20 +1,31 @@
-#include <curl/curl.h>
+#include <libgen.h>
 #include <string.h>
+#include <sys/stat.h>
+
+#include <curl/curl.h>
+#include <magic.h>
 
 #include "landerctl.h"
 
-struct curl_slist *landerctl_set_common(const landerctl_cfg *cfg, CURL *curl,
-                                        landerctl_mode mode, bool secure,
-                                        const char *key) {
-  size_t url_len = strlen(cfg->server_url) + 4;
+const char *landerctl_err_msg(landerctl_err err) {
+  switch (err) {
+  case landerctl_err_not_found:
+    return "File not found";
+  default:
+    return "";
+  }
+}
 
-  if (key != NULL) {
-    url_len += strlen(key);
+void landerctl_set_common(landerctl_ctx *ctx) {
+  size_t url_len = strlen(ctx->cfg.server_url) + 4;
+
+  if (ctx->key != NULL) {
+    url_len += strlen(ctx->key);
   }
 
   char mode_char;
 
-  switch (mode) {
+  switch (ctx->mode) {
   case landerctl_mode_short:
     mode_char = 's';
     break;
@@ -26,35 +37,85 @@ struct curl_slist *landerctl_set_common(const landerctl_cfg *cfg, CURL *curl,
     break;
   // Shouldn't be able  to happen
   default:
-    return NULL;
+    return;
   }
 
   char url[url_len + 1];
 
-  if (key == NULL) {
-    sprintf(url, "%s/%c%s/", cfg->server_url, mode_char, secure ? "l" : "");
+  if (ctx->key == NULL) {
+    sprintf(url, "%s/%c%s/", ctx->cfg.server_url, mode_char,
+            ctx->secure ? "l" : "");
   } else {
-    sprintf(url, "%s/%c%s/%s", cfg->server_url, mode_char, secure ? "l" : "",
-            key);
+    sprintf(url, "%s/%c%s/%s", ctx->cfg.server_url, mode_char,
+            ctx->secure ? "l" : "", ctx->key);
   }
 
-  curl_easy_setopt(curl, CURLOPT_URL, url);
+  curl_easy_setopt(ctx->curl, CURLOPT_URL, url);
 
   // Add API key header
-  char api_key_header[strlen(cfg->api_key) + 12];
-  sprintf(api_key_header, "X-Api-Key: %s", cfg->api_key);
+  char api_key_header[strlen(ctx->cfg.api_key) + 12];
+  sprintf(api_key_header, "X-Api-Key: %s", ctx->cfg.api_key);
 
-  struct curl_slist *list = NULL;
-  list = curl_slist_append(list, api_key_header);
+  ctx->headers = curl_slist_append(NULL, api_key_header);
 
-  curl_easy_setopt(curl, CURLOPT_HTTPHEADER, list);
-
-  curl_easy_setopt(curl, CURLOPT_USERAGENT, "landerctl/" LANDER_VERSION "");
-
-  return list;
+  curl_easy_setopt(ctx->curl, CURLOPT_USERAGENT,
+                   "landerctl/" LANDER_VERSION "");
 }
 
-void landerctl_post_short(CURL *curl, const char *url) {
-  curl_easy_setopt(curl, CURLOPT_POSTFIELDSIZE, strlen(url));
-  curl_easy_setopt(curl, CURLOPT_POSTFIELDS, url);
+landerctl_err landerctl_post_short(landerctl_ctx *ctx) {
+  curl_easy_setopt(ctx->curl, CURLOPT_POSTFIELDSIZE, strlen(ctx->arg));
+  curl_easy_setopt(ctx->curl, CURLOPT_POSTFIELDS, ctx->arg);
+
+  return landerctl_err_ok;
+}
+
+landerctl_err landerctl_post_paste(landerctl_ctx *ctx) {
+  ctx->data_file = fopen(ctx->arg, "rb");
+
+  if (ctx->data_file == NULL) {
+    return landerctl_err_not_found;
+  }
+
+  struct stat sb;
+  stat(ctx->arg, &sb);
+
+  curl_easy_setopt(ctx->curl, CURLOPT_POST, 1L);
+  curl_easy_setopt(ctx->curl, CURLOPT_READDATA, ctx->data_file);
+  curl_easy_setopt(ctx->curl, CURLOPT_POSTFIELDSIZE, sb.st_size);
+
+  return landerctl_err_ok;
+}
+
+landerctl_err landerctl_post_file(landerctl_ctx *ctx) {
+  ctx->data_file = fopen(ctx->arg, "rb");
+
+  if (ctx->data_file == NULL) {
+    return landerctl_err_not_found;
+  }
+
+  struct stat sb;
+  stat(ctx->arg, &sb);
+
+  curl_easy_setopt(ctx->curl, CURLOPT_POST, 1L);
+  curl_easy_setopt(ctx->curl, CURLOPT_READDATA, ctx->data_file);
+  curl_easy_setopt(ctx->curl, CURLOPT_POSTFIELDSIZE_LARGE, sb.st_size);
+
+  magic_t cookie = magic_open(MAGIC_MIME_TYPE);
+  magic_load(cookie, NULL);
+  const char *mime_type = magic_file(cookie, ctx->arg);
+
+  char content_type_header[strlen(mime_type) + 24];
+  sprintf(content_type_header, "X-Lander-Content-Type: %s", mime_type);
+
+  char s[strlen(ctx->arg) + 1];
+  strcpy(s, ctx->arg);
+  const char *base_name = basename(s);
+
+  char filename_header[strlen(base_name) + 20];
+  sprintf(filename_header, "X-Lander-Filename: %s", base_name);
+
+  ctx->headers = curl_slist_append(ctx->headers, content_type_header);
+  ctx->headers = curl_slist_append(ctx->headers, filename_header);
+
+  return landerctl_err_ok;
 }