diff --git a/src/pacman/conf.h b/src/pacman/conf.h
index 2c4fddf0..8c53f9cc 100644
--- a/src/pacman/conf.h
+++ b/src/pacman/conf.h
@@ -59,6 +59,7 @@ typedef struct __config_t {
 	unsigned short color;
 	unsigned short disable_dl_timeout;
 	unsigned short disable_sandbox;
+	unsigned short retry_input;
 	char *print_format;
 	/* unfortunately, we have to keep track of paths both here and in the library
 	 * because they can come from both the command line or config file, and we
@@ -214,7 +215,8 @@ enum {
 	OP_REFRESH,
 	OP_ASSUMEINSTALLED,
 	OP_DISABLEDLTIMEOUT,
-	OP_DISABLESANDBOX
+	OP_DISABLESANDBOX,
+	OP_RETRYINPUT
 };
 
 /* clean method */
diff --git a/src/pacman/pacman.c b/src/pacman/pacman.c
index 2866fc98..a4c829f1 100644
--- a/src/pacman/pacman.c
+++ b/src/pacman/pacman.c
@@ -228,6 +228,7 @@ static void usage(int op, const char * const myname)
 		          "                       use relaxed timeouts for download\n"));
 		addlist(_("      --disable-sandbox\n"
 		          "                       disable the sandbox used for the downloader process\n"));
+		addlist(_("      --retry-prompt   repeat prompts until a valid answer is supplied\n"));
 	}
 	list = alpm_list_msort(list, alpm_list_count(list), options_cmp);
 	for(i = list; i; i = alpm_list_next(i)) {
@@ -499,6 +500,9 @@ static int parsearg_global(int opt)
 		case 'v':
 			(config->verbose)++;
 			break;
+		case OP_RETRYINPUT:
+			config->retry_input = 1;
+			break;
 		default:
 			return 1;
 	}
@@ -982,6 +986,7 @@ static int parseargs(int argc, char *argv[])
 		{"color",      required_argument, 0, OP_COLOR},
 		{"disable-download-timeout", no_argument, 0, OP_DISABLEDLTIMEOUT},
 		{"disable-sandbox", no_argument, 0, OP_DISABLESANDBOX},
+		{"retry-prompt", no_argument, 0, OP_RETRYINPUT},
 		{0, 0, 0, 0}
 	};
 
diff --git a/src/pacman/po/de.po b/src/pacman/po/de.po
index 1d5d9e12..146b0b54 100644
--- a/src/pacman/po/de.po
+++ b/src/pacman/po/de.po
@@ -1317,6 +1317,13 @@ msgid ""
 "      --disable-sandbox\n"
 "                       disable the sandbox used for the downloader process\n"
 msgstr ""
+"     --disable-sandbox\n"
+"                      shaltet Sandbox für den Download-Prozess aus\n"
+
+#: src/pacman/pacman.c:231
+#, c-format
+msgid "      --retry-prompt   repeat prompts until a valid answer is supplied\n"
+msgstr "      --retry-prompt   wiederholt Frage, bis eine valide Antwort gegeben wird\n"
 
 #: src/pacman/pacman.c:249
 #, c-format
@@ -1866,6 +1873,11 @@ msgstr "[J/n]"
 msgid "[y/N]"
 msgstr "[j/N]"
 
+#: src/pacman/util.c:1741
+#, c-format
+msgid "vsnprintf failure: Failed to cache prompt: %s\n"
+msgstr "vsnprintf-fehler: Kann Frage nicht cachen: %s\n"
+
 #: src/pacman/util.c:1751
 #, c-format
 msgid "Y"
@@ -1886,6 +1898,11 @@ msgstr "N"
 msgid "NO"
 msgstr "NEIN"
 
+#: src/pacman/util.c:1769
+#, c-format
+msgid "vsnprintf failure: Failed to cache prompt: Required size changed: %zu -> %i bytes\n"
+msgstr "vsnprintf-fehler: Kann Frage nicht cachen: Benötigte Größe hat sich geändert: %zu -> %i bytes\n"
+
 #: src/pacman/util.c:1820
 #, c-format
 msgid "failed to allocate string\n"
diff --git a/src/pacman/po/en_GB.po b/src/pacman/po/en_GB.po
index 11664de1..0189ec22 100644
--- a/src/pacman/po/en_GB.po
+++ b/src/pacman/po/en_GB.po
@@ -1232,6 +1232,11 @@ msgstr ""
 "      --disable-sandbox\n"
 "                       disable the sandbox used for the downloader process\n"
 
+#: src/pacman/pacman.c:231
+#, c-format
+msgid "      --retry-prompt   repeat prompts until a valid answer is supplied\n"
+msgstr "      --retry-prompt   repeat prompts until a valid answer is supplied\n"
+
 #: src/pacman/pacman.c:249
 #, c-format
 msgid ""
@@ -1777,6 +1782,10 @@ msgstr "[Y/n]"
 msgid "[y/N]"
 msgstr "[y/N]"
 
+#: src/pacman/util.c:1741 src/pacman/util.c:1759
+msgid "vsnprintf failure: Failed to cache prompt: %s\n"
+msgstr "vsnprintf failure: Failed to cache prompt: %s\n"
+
 #: src/pacman/util.c:1751
 #, c-format
 msgid "Y"
@@ -1797,6 +1806,11 @@ msgstr "N"
 msgid "NO"
 msgstr "NO"
 
+#: src/pacman/util.c:1767
+#, c-format
+msgid "vsnprintf failure: Failed to cache prompt: Required size changed: %zu -> %i bytes\n"
+msgstr "vsnprintf failure: Failed to cache prompt: Required size changed: %zu -> %i bytes\n"
+
 #: src/pacman/util.c:1820
 #, c-format
 msgid "failed to allocate string\n"
diff --git a/src/pacman/util.c b/src/pacman/util.c
index 3b96568d..d8803cf6 100644
--- a/src/pacman/util.c
+++ b/src/pacman/util.c
@@ -1706,10 +1706,19 @@ static int mbscasecmp(const char *s1, const char *s2)
 __attribute__((format(printf, 2, 0)))
 static int question(short preset, const char *format, va_list args)
 {
+	int return_code = 0;
 	char response[32];
 	FILE *stream;
 	int fd_in = fileno(stdin);
 
+	va_list args_copy;
+	int     format_len;
+	/* No need to initialize:
+	 * the other calls also print a termination character */
+	char    prompt_cache_stack[256];
+	char   *prompt_cache      = prompt_cache_stack;
+	size_t  prompt_cache_size = sizeof(prompt_cache_stack);
+
 	if(config->noconfirm) {
 		stream = stdout;
 	} else {
@@ -1717,48 +1726,110 @@ static int question(short preset, const char *format, va_list args)
 		stream = stderr;
 	}
 
-	/* ensure all text makes it to the screen before we prompt the user */
-	fflush(stdout);
-	fflush(stderr);
+	/* Cache prompt, because we can't call v*printf() multiple times
+	 * on the same arguments. */
+	/* Copy args so we can retry when the buffer is too small */
+	va_copy(args_copy, args);
 
-	fputs(config->colstr.colon, stream);
-	vfprintf(stream, format, args);
+	/* Don't ask me why v*printf() returns an Integer instead of a long */
+	format_len = vsnprintf(
+			prompt_cache,
+			prompt_cache_size,
+			format, args);
 
-	if(preset) {
-		fprintf(stream, " %s ", _("[Y/n]"));
-	} else {
-		fprintf(stream, " %s ", _("[y/N]"));
+	/* Something has gone wrong */
+	if (format_len < 1) {
+		pm_printf(ALPM_LOG_ERROR, _("vsnprintf failure: Failed to cache prompt: %s\n"), strerror(errno));
+
+		goto free_args_copy;
 	}
 
-	fputs(config->colstr.nocolor, stream);
-	fflush(stream);
+	/* Buffer is too small */
+	if ((size_t)format_len + 1 > prompt_cache_size) {
+		prompt_cache = malloc(format_len + 1);
+		prompt_cache_size = format_len + 1;
+		if (prompt_cache == 0) {
+			pm_printf(ALPM_LOG_ERROR, _("malloc failure: could not allocate %i bytes\n"), format_len + 1);
 
-	if(config->noconfirm) {
-		fprintf(stream, "\n");
-		return preset;
+			goto free_args_copy;
+		}
+
+		format_len = vsnprintf(prompt_cache, prompt_cache_size, format, args_copy);
+		/* Something has gone wrong */
+		if (format_len < 1) {
+			pm_printf(ALPM_LOG_ERROR, _("vsnprintf failure: Failed to cache prompt: %s\n"), strerror(errno));
+
+			goto free_args_copy;
+		}
+
+		/* Just in case */
+		if ((size_t)format + 1 != prompt_cache_size) {
+			pm_printf(ALPM_LOG_ERROR, _("vsnprintf failure: Failed to cache prompt: Required size changed: %zu -> %i bytes\n"), prompt_cache_size, format_len + 1);
+
+			goto free_args_copy;
+		}
 	}
 
-	flush_term_input(fd_in);
+	/* We can free the argument-copy now */
+	va_end(args_copy);
 
-	if(safe_fgets_stdin(response, sizeof(response))) {
-		size_t len = strtrim(response);
-		if(len == 0) {
+	/* Prompt the user at least once before exiting */
+	do {
+		/* Ensure all text makes it to the screen before we prompt the user */
+		fflush(stdout);
+		fflush(stderr);
+
+		fputs(config->colstr.colon, stream);
+		fputs(prompt_cache, stream);
+
+		if(preset) {
+			fprintf(stream, " %s ", _("[Y/n]"));
+		} else {
+			fprintf(stream, " %s ", _("[y/N]"));
+		}
+
+		fputs(config->colstr.nocolor, stream);
+		fflush(stream);
+
+		if(config->noconfirm) {
+			fprintf(stream, "\n");
 			return preset;
 		}
 
-		/* if stdin is piped, response does not get printed out, and as a result
-		 * a \n is missing, resulting in broken output */
-		if(!isatty(fd_in)) {
-			fprintf(stream, "%s\n", response);
-		}
+		flush_term_input(fd_in);
 
-		if(mbscasecmp(response, _("Y")) == 0 || mbscasecmp(response, _("YES")) == 0) {
-			return 1;
-		} else if(mbscasecmp(response, _("N")) == 0 || mbscasecmp(response, _("NO")) == 0) {
-			return 0;
+		if(safe_fgets_stdin(response, sizeof(response))) {
+			size_t len = strtrim(response);
+			if(len == 0) {
+				return_code = preset;
+				goto opt_free_cache;
+			}
+
+			/* if stdin is piped, response does not get printed out, and as a result
+			 * a \n is missing, resulting in broken output */
+			if(!isatty(fd_in)) {
+				fprintf(stream, "%s\n", response);
+			}
+
+			if(mbscasecmp(response, _("Y")) == 0 || mbscasecmp(response, _("YES")) == 0) {
+				return_code = 1;
+				goto opt_free_cache;
+			} else if(mbscasecmp(response, _("N")) == 0 || mbscasecmp(response, _("NO")) == 0) {
+				goto opt_free_cache;
+			} else
+				/* Emulate same behaviour as multiselect_question() and select_question() */
+				fprintf(stream, _("invalid input: prompt requires `%s' or `%s'\n\n"), _("Y"), _("N"));
 		}
-	}
-	return 0;
+	} while (config->retry_input);
+
+opt_free_cache:
+	if (prompt_cache != prompt_cache_stack)
+		free(prompt_cache);
+	return return_code;
+
+free_args_copy:
+	va_end(args_copy);
+	return return_code;
 }
 
 int yesno(const char *format, ...)