Praise be to Allah.
Firstly:
If a person passes the miqaat intending to do Hajj or ‘umrah, it is not permissible for him to pass it without entering ihram, because of the report narrated by Ibn ‘Abbaas (may Allah be pleased with him) who said: The Messenger of Allaah (peace and blessings of Allaah be upon him) defined the meeqaat of the people of Madeenah as Dhu’l-Hulayfah; that of the people of Shaam (Syria) as al-Juhfah; that of the people of Najd as Qarn al-Manaazil; and that of the people of Yemen as Yalamlam. And he said: “And these miqaats are for the people at those very places, and besides them for those who come through those places, and are not residents thereof, with the intention of performing Hajj and ‘Umrah; and whoever is living within these boundaries can enter ihraam from the place where he lives, and the people of Makkah can start from Makkah.”
Narrated by al-Bukhaari, 1526; Muslim, 1181
An-Nawawi (may Allah have mercy on him) said: ash-Shaafa‘i and our companions said: If the one who has come from far away comes to the miqaat intending to perform Hajj or ‘Umrah or qiraan (i.e., both), it is haraam for him to pass it without entering ihram, according to scholarly consensus.
End quote from al-Majmoo‘, 7/214
But if he passed the miqaat without intending to do Hajj or ‘umrah, or he was not sure and had not yet made up his mind, then he decided to do ‘umrah after passing the miqaat, he should enter ihram from the place where he decided to do ‘umrah, unless he is in Makkah, in which case he should go outside of the Haram zone then enter ihram for ‘umrah from there.
Al-Haafiz Ibn Hajar (may Allah have mercy on him) said, commenting on the hadeeth of Ibn ‘Abbaas quoted above:
From this we understand that if a person travels without the intention of doing Hajj or ‘umrah and he passes the miqaat, then after that he decides to do Hajj or ‘umrah, he should enter ihram from the place where he decided to do Hajj or ‘umrah, and he does not have to go back to the miqaat, because the Prophet (blessings and peace of Allah be upon him) said: “from the place he sets out”.
End quote from Fath al-Baari
Shaykh Muhammad al-Mukhtaar ash-Shanqeeti (may Allah preserve him) said:
The second scenario: if he went to Jeddah and was hesitant, thinking: I do not know if I will have enough time or not, then in such cases it is permissible for him not to enter ihram at the miqaat of Madinah.
For example: there is a person who has some business to do in Jeddah and he does not know whether he will have enough time to do ‘umrah or not. If he is not sure about the time, it is permissible for him to go to Jeddah without ihram, and do what he needs to in Jeddah, then enter ihram from Jeddah if he decides to go to ‘umrah from there, because the Prophet (blessings and peace of Allah be upon him) said: “and whoever is living within these boundaries can enter ihraam from the place he decides (to do ‘umrah).”
This applies to the one who does not have the clear intention of performing ‘umrah from Madinah, so he is uncertain and hesitant; he does not have to enter ihram until he is certain that he is going to do ‘umrah.
End quote from Sharh Zaad al-Mustaqni‘.
Shaykh ‘Abd al-‘Azeez ibn ‘Abdullah ibn Aal ash-Shaykh (may Allah preserve him) was asked:
My colleagues and I were sent to Jeddah to do work for Hajj for two months. Some of us put our ihram in our cars or suitcases, then when we found some free time we intended to do ‘Umrah and entered ihram from Jeddah. Is this permissible, or do we have to go to the miqaat of as-Sayl and enter ihram from there?
He replied: If you had decided to do ‘umrah before travelling, and from the time you started your journey to Jeddah your intention was to do ‘umrah, then what you have to do is enter ihram from the miqaat, because the intention to do ‘umrah had already been formed. But if the decision to do ‘umrah was not made until after you had settled in Jeddah, then you should enter ihram from Jeddah.
But if your intention was not fixed, in the sense that you were not sure, then this uncertainty means that you had not firmly decided to do ‘umrah. Based on that, if you made your mind up when you were closer (to Makkah) than the miqaat, you can enter ihram from the place where you formed your intention. And Allah knows best.
End quote from Majallat al-Buhooth al-Islamiyyah, 60/95
Secondly:
If a person passes the miqaat, intending to do Hajj or ‘umrah, then he does not enter ihram from the miqaat, he has to go back to the miqaat that he passed and enter ihram from there. If he does not go back, he has to offer a sacrifice for each time that he passed it.
Shaykh Ibn Baaz (may Allah have mercy on him) was asked about a person who was obliged to offer a sacrifice because he entered ihram from Jeddah after passing the miqaat, and he has made this mistake several times – what does he have to do? Should he offer one sacrifice and will that be sufficient, or is the answer something other than that?
He replied: He has to offer a sacrifice for each occasion, to be slaughtered in Makkah for the poor, if he passed the miqaat intending to do Hajj or ‘umrah, then he entered ihram from Jeddah. One seventh of a camel or one seventh of a cow is acceptable as a sacrifice for that. He also has to repent to Allah, may He be glorified, from that, because it is not permissible for a Muslim to pass the miqaat, intending to do Hajj or ‘Umrah, without entering ihraam, because the Prophet (blessings and peace of Allah be upon him) said: “And these miqaats are for the people at those very places, and besides them for those who come through those places, and are not residents thereof, with the intention of performing Hajj and ‘Umrah”; and because Ibn ‘Abbaas (may Allah be pleased with him) said: Whoever omits a ritual (of Hajj or ‘umrah) or forgets it, let him offer a sacrifice.
End quote from Majmoo‘ al-Fataawa, 17/12
He has to try hard to remember how many times he has to offer sacrifices for, until he thinks it most likely that he has discharged his duty.
Thirdly:
If a woman sees the tuhr (signal of the end of menses) that she usually sees at the end of her period, whether that is complete dryness or the white discharge, whatever usually signals the end of her period, and she purifies herself and does tawaaf (circumambulation of the Ka‘bah) and sa‘i (going between as-Safa and al-Marwah), or prays and fasts, then after that she becomes uncertain about the state of purity on which she based those acts of worship, she should not pay any attention to that uncertainty and she does not have to do anything, because uncertainty after completing an act of worship does not have any impact, so long as she started it when she was certain about her situation, on the basis of what she usually sees at the end of her menses.
But if she was hasty and was not sure whether her menses had ended before she started ‘umrah, and she did not sees what she usually sees every time her period ends, then after that she began to doubt whether her menses had ended, as is the case in this question, then her ‘umrah is not complete, because the basic principle is that she was still menstruating and she did not know whether her period has ended. So she has to avoid all the things that are prohibited during ihram, the most important of which is intercourse with her husband, because she is still in a state of ihram until she goes back to Makkah, does tawaaf and saa‘i, and cuts her hair, then exits her ihram.
If she did any of the actions that are prohibited during ihram before that, she is excused for them because she thought that her ‘umrah had ended.
Shaykh Ibn ‘Uthaymeen (may Allah have mercy on him) said: With regard to what she has done of the things that are prohibited (during ihram), let us assume that her husband had intercourse with her, and intercourse during ihram is the most serious of the prohibited actions; however there is no blame on her because she was unaware of the ruling. If a person does one of the actions that are prohibited during ihram out of ignorance or because he forgot or was forced to do it, there is no blame on him.
End quote from Majmoo‘ al-Fataawa, 21/351
And Allah knows best.
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