diff --git a/channels/chan_dahdi.c b/channels/chan_dahdi.c
index e49a7996a9..8897bb6954 100644
--- a/channels/chan_dahdi.c
+++ b/channels/chan_dahdi.c
@@ -13178,7 +13178,8 @@ static struct dahdi_pvt *mkintf(int channel, const struct dahdi_chan_conf *conf,
 				analog_p->canpark = conf->chan.canpark;
 				analog_p->dahditrcallerid = conf->chan.dahditrcallerid;
 				analog_p->immediate = conf->chan.immediate;
-				analog_p->permhidecallerid = conf->chan.permhidecallerid;
+				analog_p->permhidecallerid = conf->chan.hidecallerid; /* hidecallerid is the config setting, not permhidecallerid (~permcallwaiting above) */
+				/* It's not necessary to set analog_p->hidecallerid here, sig_analog will set hidecallerid=permhidecaller before each call */
 				analog_p->pulse = conf->chan.pulse;
 				analog_p->threewaycalling = conf->chan.threewaycalling;
 				analog_p->transfer = conf->chan.transfer;
diff --git a/channels/sig_analog.c b/channels/sig_analog.c
index 5ae96d9418..8d5ccd64fc 100644
--- a/channels/sig_analog.c
+++ b/channels/sig_analog.c
@@ -1451,6 +1451,8 @@ int analog_hangup(struct analog_pvt *p, struct ast_channel *ast)
 		ast_channel_setoption(ast,AST_OPTION_TDD,&x,sizeof(char),0);
 		p->callwaitcas = 0;
 		analog_set_callwaiting(p, p->permcallwaiting);
+		/* In theory, the below is not necessary since we set hidecallerid = permhidecaller when calls start,
+		 * but this ensures the setting is defaulted properly when channels are idle, too. */
 		p->hidecallerid = p->permhidecallerid;
 		analog_set_dialing(p, 0);
 		analog_update_conf(p);
@@ -2133,6 +2135,19 @@ static void *__analog_ss_thread(void *data)
 	case ANALOG_SIG_FXOLS:
 	case ANALOG_SIG_FXOGS:
 	case ANALOG_SIG_FXOKS:
+		/* Set our default presentation.
+		 * This is necessary because the presentation for each call is independent
+		 * (though the default may be the same).
+		 * For example, if hidecallerid=yes and somebody makes a call with *82,
+		 * then makes a 3-way call, the presentation for the 2nd call should still
+		 * be blocked, unless that also had a *82.
+		 * For this reason, setting hidecallerid = permhidecallerid on hangup
+		 * is NOT sufficient, as the *82 from the first call could "leak" into
+		 * subsequent ones made before a hangup, improperly leaking a number
+		 * that should have been hidden.
+		 */
+		p->hidecallerid = p->permhidecallerid;
+
 		/* Read the first digit */
 		timeout = analog_get_firstdigit_timeout(p);
 		/* If starting a threeway call, never timeout on the first digit so someone
@@ -2190,18 +2205,18 @@ static void *__analog_ss_thread(void *data)
 						res = analog_play_tone(p, idx, -1);
 						ast_channel_lock(chan);
 						ast_channel_exten_set(chan, exten);
-						if (!ast_strlen_zero(p->cid_num)) {
-							if (!p->hidecallerid) {
-								ast_set_callerid(chan, p->cid_num, NULL, p->cid_num);
-							} else {
-								ast_set_callerid(chan, NULL, NULL, p->cid_num);
-							}
-						}
-						if (!ast_strlen_zero(p->cid_name)) {
-							if (!p->hidecallerid) {
-								ast_set_callerid(chan, NULL, p->cid_name, NULL);
-							}
+
+						/* Properly set the presentation.
+						 * We need to do this here as well, because p->hidecallerid might be set
+						 * due to permanent blocking, not star-67/star-82 usage. */
+						if (p->hidecallerid) {
+							ast_channel_caller(chan)->id.number.presentation = AST_PRES_PROHIB_USER_NUMBER_NOT_SCREENED;
+							ast_channel_caller(chan)->id.name.presentation = AST_PRES_PROHIB_USER_NUMBER_NOT_SCREENED;
+						} else {
+							ast_channel_caller(chan)->id.number.presentation = AST_PRES_ALLOWED_USER_NUMBER_NOT_SCREENED;
+							ast_channel_caller(chan)->id.name.presentation = AST_PRES_ALLOWED_USER_NUMBER_NOT_SCREENED;
 						}
+
 						ast_setstate(chan, AST_STATE_RING);
 						ast_channel_unlock(chan);
 						analog_set_echocanceller(p, 1);
@@ -2263,9 +2278,11 @@ static void *__analog_ss_thread(void *data)
 					ast_hangup(chan);
 					goto quit;
 				}
-
+			/* While the DMS-100 allows dialing as many *67s and *82s in succession as one's heart may desire,
+			 * the 5ESS does not, it only allows pure toggling (and only once!). So, it's not incorrect
+			 * to prevent people from dialing *67 if that won't actually do anything. */
 			} else if (!p->hidecallerid && !strcmp(exten, "*67")) {
-				ast_verb(3, "Disabling Caller*ID on %s\n", ast_channel_name(chan));
+				ast_verb(3, "Blocking Caller*ID on %s\n", ast_channel_name(chan));
 				/* Disable Caller*ID if enabled */
 				p->hidecallerid = 1;
 				ast_channel_caller(chan)->id.number.presentation = AST_PRES_PROHIB_USER_NUMBER_NOT_SCREENED;
@@ -2352,7 +2369,7 @@ static void *__analog_ss_thread(void *data)
 					len = 0;
 				}
 			} else if (p->hidecallerid && !strcmp(exten, "*82")) {
-				ast_verb(3, "Enabling Caller*ID on %s\n", ast_channel_name(chan));
+				ast_verb(3, "Allowing Caller*ID on %s\n", ast_channel_name(chan));
 				/* Enable Caller*ID if enabled */
 				p->hidecallerid = 0;
 				ast_channel_caller(chan)->id.number.presentation = AST_PRES_ALLOWED_USER_NUMBER_NOT_SCREENED;