The second exception to the plain meaning rule has likewise been long-standing: that evidence of the circumstances surrounding and informing the testator’s situation is admissible if there is an ambiguity regardless of whether that ambiguity is latent or patent:
(b) Qualifications and true scope of (plain meaning) rule
The statement of the rule given in the next preceding subdivision is too broad, and has led to much confusion among the courts. No such unqualified rule can stand in the face of the numerous cases admitting some extrinsic evidence where the indefiniteness, inaccuracy, or ambiguity was apparent on the face of the instrument.
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According to the better view, or the more accurate statement of the true rule, extrinsic evidence is admissible to show the situation of the testator and all the relevant facts and circumstances surrounding him at the time of the making of the will, for the purpose of explaining or resolving even a patent ambiguity.
This evidence frames the settlor’s point of view when he or she drafts the document:
Of the competency of this evidence there can be no doubt. The purpose of it was to place the court, as far as possible, in the situation in which the testator stood, and thus bring the words employed by him into contact with the circumstances attending the execution of the will. Such proof does not contradict the terms of that instrument, nor tend to wrest the words of the testator from their natural operation. It serves only to identify the institutions described by him as ‘the Board of Foreign and the Board of Home Missions;’ and thus the court is enabled to avail itself of the light which the circumstances in which the testator was placed at the time he made the will would throw upon his intention. ‘The law is not so unreasonable,’ says Mr. Wigram, ‘as to deny to the reader of an instrument the same light which the writer enjoyed.’ Wig. Wills, (2d Amer. Ed.) 161.
Thus Courts look to the particular circumstances of a decedent to ascertain the “plain meaning” of the words used: “If we put ourselves, in the traditional place, behind the armchair of the testator as he contemplates the disposition he wished to be made to the objects of his bounty, we would be standing behind a man who was not unaware of the problems and methods of early, as contrasted to late, vesting of trust estates and one upon whom had been urged the desirability of continuing property in trust.” Also: “Sitting in Loretta’s armchair, her testamentary intent becomes clear …”
This exception to the plain meaning rule that enables the Courts to sit in a testator’s “armchair” does not permit direct evidence of intent by extrinsic evidence but may yield a close approximation. In one Maryland case, for example, the Court addressed the meaning of the phrase “upon the youngest living grandchild (of the testator’s sister) … attaining the age of twenty-one years” in a testamentary trust. The Court concluded that the phrase could have one of two different interpretations – vesting when the sister’s grandchildren then in being had all reach twenty-one years of age as of any point in time or, effectively measured after all of the sister’s children had died (thus closing the class) and then waiting for the youngest to reach twenty-one years of age. The Court opted for the second reading based on the extrinsic evidence of the testator’s situation. This evidence concluded that early vesting had caused adverse tax issues in his mother’s estate and that he was urged, upon receiving assets from his family, to continue those assets in trust. Examining the circumstances at the time of the execution of his will in order to place the Court in his “armchair” at the critical moment, required that extensive extrinsic evidence be entertained in order to interpret what certain words in his testamentary trust meant. In a word, it established his intent as that intent was expressed in the language of the trust. This was not a case where the Court found a latent ambiguity.
 Gilmer v. Stone, 120 U.S. 586, 590, 7 S.Ct. 689, 690 (1887).
 Marty v. First Nat. Bank of Baltimore, 209 Md. 210, 218, 120 A.2d 841, 845 (1956).
 Bregel v. Julier, 253 Md. 103, 111, 251 A.2d 891, 895 (1969).
 Marty v. First Nat. Bank of Baltimore, 209 Md. 210, 120 A.2d 841 (1956).